CN109873086A - A kind of cross-linking hole transport layer material and preparation method thereof - Google Patents
A kind of cross-linking hole transport layer material and preparation method thereof Download PDFInfo
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- CN109873086A CN109873086A CN201910145196.6A CN201910145196A CN109873086A CN 109873086 A CN109873086 A CN 109873086A CN 201910145196 A CN201910145196 A CN 201910145196A CN 109873086 A CN109873086 A CN 109873086A
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Abstract
The application provides a kind of cross-linking hole transport layer material and preparation method thereof, applied in OLED display panel, OLED display panel includes the OLED device being made on underlay substrate at underlay substrate and interval, and OLED device includes cathode, hole transmission layer, luminescent layer, electron transfer layer, anode；Wherein, the preparation method of hole transmission layer includes: offer precursor solution comprising precursor molecule and organic solvent, precursor molecule are Porphyrin Molecule or Phthalocyanine, include crosslinked group in precursor molecule；Precursor solution is prepared on cathode, it is hole transmission layer that heat treatment, which makes precursor solution crosslink reaction to form uniform and stable thin polymer film, to effectively improve the interfacial property of inkjet printing device, further promotes the performance of device.
Description
Technical field
This application involves field of display technology more particularly to a kind of cross-linking hole transport layer material and preparation method thereof.
Background technique
Solution process OLED device, especially inkjet printing OLED device, since it is in large area panel preparation process
Low cost, the advantage without metallic mask and high stock utilization receive more and more concerns.It is known that OLED device
Include multilayered structure in part: luminescent layer (EML), electron transfer layer (ETL), hole transmission layer (HTL) etc., therefore how in device
The intersolubility that different function interlayer is solved the problems, such as in the preparation process of part is always a big challenge.Utilize orthogonal solvent system
This problem can be alleviated to a certain extent, however most of organic material also has certain dissolution in the solvent of upper layer
Property, this is just that the selection of orthogonal solvent system brings very big difficulty.
Therefore, the prior art is defective, needs to improve.
Summary of the invention
The application provides a kind of cross-linking hole transport layer material and preparation method thereof, can efficiently solve different function
The problem of dissolving each other between layer, effectively improves the interfacial property of inkjet printing device, to promote the performance of device.
To solve the above problems, technical solution provided by the present application is as follows:
The application provides a kind of preparation method of cross-linking hole transport layer material, is applied in OLED display panel, institute
State the OLED device being made on the underlay substrate that OLED display panel includes underlay substrate and interval, the OLED device
Including cathode, hole transmission layer, luminescent layer, electron transfer layer, anode；
The preparation method of the hole transmission layer includes:
Precursor solution is provided, the precursor solution includes precursor molecule and organic solvent, and the precursor molecule is porphin
Quinoline molecule or Phthalocyanine include crosslinked group in the precursor molecule；
The precursor solution is prepared on the cathode, heat treatment makes the precursor solution crosslink reaction shape
It is the hole transmission layer at thin polymer film.
In the preparation method of the application, the preparation method of the precursor solution includes:
The precursor molecule is added in the organic solvent, it is described organic molten that stirring is dissolved to the precursor molecule
In agent, surface tension modifier and viscosity modifier is added, the precursor solution is made to can satisfy the demand of inkjet printing.
In the preparation method of the application, the organic solvent includes arene, ethers, at least one in esters solvent
Kind.
It include indone and butyl methyl phenyl ethers anisole in the organic solvent in the preparation method of the application.
In the preparation method of the application, the surface tension modifier include imidazoles, imdazole derivatives, phenol, to benzene
One of diphenol or more than one；The viscosity modifier include one of alcohol, ether, ester, phenol, amine or more than one.
It further include bridged group, substituent group, the bridging group in the precursor molecule in the preparation method of the application
Group includes trianilino group or carbazoles group, and the substituent group includes alkyl or tert-butyl, and the crosslinked group includes pair
Styrene group.
In the preparation method of the application, it the described method comprises the following steps:
Step S10 provides a underlay substrate, and pixel defining layer, the pixel defining layer are formed on the underlay substrate
Pixel region is defined, the corresponding pixel region forms the cathode of array distribution；
Step S20, provides precursor solution, and the precursor solution is prepared on the cathode, and heat treatment makes described
Precursor solution crosslinks the thin polymer film that reaction forms the corresponding pixel region, and the thin polymer film is hole
Transport layer；
Step S30 sequentially forms luminescent layer, electron transfer layer and anode on the hole transport layer, with formation pair
Answer the OLED device of the pixel region.
To solve the above problems, the application also provides a kind of cross-linking hole transport layer material, it is applied to OLED display surface
In plate, the OLED display panel includes the OLED device being made on the underlay substrate at underlay substrate and interval, described
OLED device includes cathode, hole transmission layer, luminescent layer, electron transfer layer, anode；
The hole transmission layer is the thin polymer film formed after reaction in-situ is crosslinked by precursor solution, the forerunner
It include precursor molecule and organic solvent in liquid solution, the precursor molecule is Porphyrin Molecule or Phthalocyanine, the precursor molecule
In include crosslinked group.
In the cross-linking hole transport layer material of the application, the OLED device is inverted OLED device, described
OLED display panel further includes pixel defining layer, is set on the underlay substrate, and define pixel region；The OLED device
The corresponding pixel region setting.
In the cross-linking hole transport layer material of the application, the organic solvent includes that arene, ethers, esters are molten
At least one of agent；It further include bridged group, substituent group in the precursor molecule, the bridged group includes triphenylamine base
Group or carbazoles group, the substituent group include alkyl or tert-butyl, and the crosslinked group includes to styrene group.
The application's has the beneficial effect that, compared to existing OLED display panel, cross-linking hole provided by the present application passes
Defeated layer material and preparation method thereof utilizes the side of reaction in-situ by providing a kind of new crosslinkable hole transport layer material
Method, forming uniform and stable thin polymer film in the cathode surface of OLED device is hole transmission layer, to effectively improve
The interfacial property of inkjet printing device further promotes the performance of device；The preparation method is simple simultaneously, and process is easily controllable.
Detailed description of the invention
It, below will be to embodiment or the prior art in order to illustrate more clearly of embodiment or technical solution in the prior art
Attached drawing needed in description is briefly described, it should be apparent that, the accompanying drawings in the following description is only some of application
Embodiment for those of ordinary skill in the art without creative efforts, can also be attached according to these
Figure obtains other attached drawings.
Fig. 1 is the preparation method stream of cross-linking hole transport layer material in OLED display panel provided by the embodiments of the present application
Cheng Tu；
Fig. 2A~2E is the preparation of cross-linking hole transport layer material in OLED display panel provided by the embodiments of the present application
Method schematic diagram.
Specific embodiment
The explanation of following embodiment is referred to the additional illustration, the particular implementation that can be used to implement to illustrate the application
Example.The direction term that the application is previously mentioned, such as [on], [under], [preceding], [rear], [left side], [right side], [interior], [outer], [side]
Deng being only the direction with reference to annexed drawings.Therefore, the direction term used be to illustrate and understand the application, rather than to
Limit the application.The similar unit of structure is with being given the same reference numerals in the figure.
The application is directed to existing OLED display panel, exists between the different function layer material of OLED device and dissolves each other
Technical problem, the present embodiment are able to solve the defect.
OLED display panel provided by the present application includes passive matrix and active array type, is shown in active array type OLED
Show in panel, the thin film transistor (TFT) (TFT) for controlling OLED device is usually made in anode side, and this requires TFT must be p
Type, and the N-shaped mobility of conventional non-crystalline silicon tft and multi-crystal TFT is significantly greater than its p-type mobility.According to inversion type
OLED device structure just can make the n-type thin film transistor of superior performance applied to the pixel of active array type OLED display panel
In circuit, the selection of active array type OLED display panel driving circuit design is increased.The present embodiment is with inversion type OLED device
It is illustrated for the OLED display panel of part structure.
Referring to Fig.1 and Fig. 2A~2E, the application provide a kind of preparation method of cross-linking hole transport layer material, application
In OLED display panel, the OLED display panel include underlay substrate 10 and interval be made on the underlay substrate 10
OLED device 30, the OLED device 30 from bottom to up include cathode 301, hole transmission layer 302, luminescent layer 303, electronics pass
Defeated layer 304, anode 305；Wherein, the preparation method of the hole transmission layer 302 includes:
Precursor solution is provided, the precursor solution includes precursor molecule and organic solvent, and the precursor molecule is porphin
Quinoline molecule or Phthalocyanine include crosslinked group in the precursor molecule；
The precursor solution is prepared on the cathode 301, it is in situ anti-that heat treatment passes through the precursor solution
It is the hole transmission layer 302 that thin polymer film, which should be cross-linked to form,.
Specifically, the structural formula of the precursor molecule is as follows:
Wherein, Ar indicates aromatic group, for providing precursor molecule skeleton, and has the function of hole transport, can be
Porphyrin group or phthalocyanines group, but not limited to this；
R1 indicates bridged group, while having stronger cavity transmission ability, can be trianilino group or carbazoles
Group, but not limited to this；
R2 indicates substituent group, and major function is to enhance the flexibility of the precursor molecule, further improves the precursor
The dissolubility and film forming of molecule, can be the groups such as alkyl or the tert-butyl of short carbon chain, but not limited to this；
R3 indicates crosslinked group, can crosslink reaction under heating or ultraviolet light (UV) radiation parameter, be used for
So that the precursor molecule is formed uniform and stable thin polymer film, can be to styrene base class group, but not limited to this.
In one embodiment, the structural formula of the precursor molecule is as follows:
Wherein, the precursor molecule includes porphyrin group and to styrene group, the double bond to styrene group
Reaction can be crosslinked after fracture.
Specifically, the preparation method of the precursor solution includes:
The precursor molecule is added in the organic solvent, it is described organic molten that stirring is dissolved to the precursor molecule
In agent, surface tension modifier and viscosity modifier is added, the precursor solution is made to can satisfy the demand of inkjet printing.
Wherein, the organic solvent includes at least one of arene, ethers, esters solvent, and but not limited to this
System.Further, the organic solvent includes but is not limited to the mixed solvent of indone and butyl methyl phenyl ethers anisole.
The surface tension modifier is one or more of small molecule compound, further, the surface tension tune
Section agent include one of imidazoles, imdazole derivatives, phenol, hydroquinone or more than one；The viscosity modifier is for adjusting
The viscosity of section system, further, the viscosity modifier include one of alcohol, ether, ester, phenol, amine or more than one.Certainly,
It can also include processing procedure acceptable other additives, such as activating agent etc. in the precursor solution.
Specifically, as shown in Figure 1, for cross-linking hole transmission layer material in OLED display panel provided by the embodiments of the present application
The preparation method flow chart of material, the described method comprises the following steps:
Step S10 provides a underlay substrate 10 in conjunction with shown in Fig. 2A, forms pixel definition on the underlay substrate 10
Layer 20, the pixel defining layer 20 define pixel region 201, and the corresponding pixel region 201 forms the cathode of array distribution
301。
Specifically, the underlay substrate 10 is the array substrate for being prepared with thin film transistor (TFT), and the thin film transistor (TFT) is n
Type.The cathode 301 is formed using the method for magnetron sputtering, and the material of the cathode 301 is transparent conductive metal oxide, such as
Tin indium oxide；Or the material of the cathode 301 is the metals such as aluminium.
Step S20 provides precursor solution in conjunction with shown in Fig. 2 B, and the precursor solution is prepared in the cathode 301
On, heat treatment makes the precursor solution crosslink the thin polymer film that reaction forms the corresponding pixel region 201, described
Thin polymer film is hole transmission layer 302.
Specifically, the precursor solution is printed in the pixel region 201 by the way of inkjet printing, then
It is dried in vacuo；Later under the conditions of heat treatment or ultraviolet light irradiation, makes the precursor solution that reaction in-situ occur and exist
It is chemically reacted in the pixel region 201；Specifically, it is anti-to participate in crosslinking for the crosslinked group in the precursor solution
The thin polymer film should be formed.
Step S30 sequentially forms luminescent layer 303, electronics on the hole transmission layer 302 in conjunction with shown in Fig. 2 C~2E
Transmitting layer 3 04 and anode 305, to form the OLED device 30 of the corresponding pixel region 201.
Specifically, the luminescent layer 303 by the methods of spin coating, inkjet printing prepare, the electron transfer layer 304 and
The anode 305 can be formed using the method for vacuum evaporation.Wherein, since the hole transmission layer 302 is thin polymer film,
Therefore there is good interfacial property, the hole transmission layer 302 is made to be provided simultaneously with good barrier property and electric conductivity, with
And good hole transport performance；Therefore, the material of the hole transmission layer 302 and the material of the luminescent layer 303 not will cause
Material will not cause the material of the hole transmission layer 302 and the material of the cathode 301 to dissolve each other there is a phenomenon where dissolving each other
The phenomenon that, to promote the performance of device.
The application also provides a kind of cross-linking hole transport layer material, be applied to OLED display panel in, in conjunction with Fig. 2A~
Shown in 2E, the OLED display panel includes: underlay substrate 10；Pixel defining layer 20 is set on the underlay substrate 10, and fixed
Justice goes out pixel region 201；The OLED device 30 being made on the underlay substrate 10 at the corresponding pixel region interval, it is described
OLED device 30 is inverted OLED device, from bottom to up successively includes cathode 301, hole transmission layer 302, luminescent layer 303, electricity
Sub- transmitting layer 3 04, anode 305.Certainly, however it is not limited to this, it may also include the conventional devices such as thin-film encapsulation layer.
Wherein, the hole transmission layer 302 is the thin polymer film formed after reaction in-situ is crosslinked by precursor solution,
In the precursor solution include precursor molecule and organic solvent, the precursor molecule be Porphyrin Molecule or Phthalocyanine, it is described
It include crosslinked group in precursor molecule.
Further, the organic solvent includes but is not limited at least one of arene, ethers, esters solvent, institute
Stating further includes bridged group, substituent group in precursor molecule, and the bridged group includes but is not limited to trianilino group or carbazole
Class group, the substituent group include but is not limited to alkyl or tert-butyl, and the crosslinked group includes but is not limited to styrene
Group.
In the present embodiment, hole transmission layer 302, institute are equipped between the cathode 301 and luminescent layer 303 in OLED device 30
It states hole transmission layer 302 and is prepared by precursor solution using the method for inkjet printing, the precursor solution can be by situ anti-
It should be cross-linked to form thin polymer film, designed by this, can effectively be promoted the comprehensive performance of the OLED device 30, especially change
Interfacial property between kind functional layer, and production method is simple.
In conclusion cross-linking hole transport layer material provided by the present application and preparation method thereof, a kind of new by providing
Crosslinkable hole transport layer material formed in the cathode surface of OLED device uniform and stable using the method for reaction in-situ
Thin polymer film be hole transmission layer, to effectively improve the interfacial property of inkjet printing device, further lifter
The performance of part；The preparation method is simple simultaneously, and process is easily controllable.
Although above preferred embodiment is not to limit in conclusion the application is disclosed above with preferred embodiment
The application processed, those skilled in the art are not departing from spirit and scope, can make various changes and profit
Decorations, therefore the protection scope of the application subjects to the scope of the claims.
Claims (10)
1. a kind of preparation method of cross-linking hole transport layer material is applied in OLED display panel, which is characterized in that described
OLED display panel includes the OLED device being made on the underlay substrate at underlay substrate and interval, the OLED device packet
Include cathode, hole transmission layer, luminescent layer, electron transfer layer, anode；
The preparation method of the hole transmission layer includes:
Precursor solution is provided, the precursor solution includes precursor molecule and organic solvent, and the precursor molecule is porphyrin point
Son or Phthalocyanine include crosslinked group in the precursor molecule；
The precursor solution is prepared on the cathode, it is poly- that heat treatment makes the precursor solution crosslink reaction formation
Closing object film is the hole transmission layer.
2. preparation method according to claim 1, which is characterized in that the preparation method of the precursor solution includes:
The precursor molecule is added in the organic solvent, stirring makes the precursor molecule be dissolved to the organic solvent
In, surface tension modifier and viscosity modifier is added, the precursor solution is made to can satisfy the demand of inkjet printing.
3. preparation method according to claim 2, which is characterized in that the organic solvent includes arene, ethers, ester
At least one of class solvent.
4. preparation method according to claim 3, which is characterized in that include indone and butyl benzene first in the organic solvent
Ether.
5. preparation method according to claim 2, which is characterized in that the surface tension modifier includes imidazoles, imidazoles
One of derivative, phenol, hydroquinone or more than one；The viscosity modifier includes alcohol, ether, ester, phenol, one in amine
Kind or more than one.
6. preparation method according to claim 1, which is characterized in that further include bridged group in the precursor molecule, take
For group, the bridged group includes trianilino group or carbazoles group, and the substituent group includes alkyl or tert-butyl, institute
Stating crosslinked group includes to styrene group.
7. preparation method according to claim 1, which is characterized in that the described method comprises the following steps:
Step S10 provides a underlay substrate, and pixel defining layer, the pixel defining layer definition are formed on the underlay substrate
Pixel region out, the corresponding pixel region form the cathode of array distribution；
Step S20, provides precursor solution, and the precursor solution is prepared on the cathode, and heat treatment makes the forerunner
Liquid solution crosslinks the thin polymer film that reaction forms the corresponding pixel region, and the thin polymer film is hole transport
Layer；
Step S30 sequentially forms luminescent layer, electron transfer layer and anode on the hole transport layer, to form corresponding institute
State the OLED device of pixel region.
8. a kind of cross-linking hole transport layer material is applied in OLED display panel, which is characterized in that the OLED display surface
Plate includes the OLED device being made on the underlay substrate at underlay substrate and interval, and the OLED device includes cathode, sky
Cave transport layer, luminescent layer, electron transfer layer, anode；
The hole transmission layer is the thin polymer film formed after reaction in-situ is crosslinked by precursor solution, and the presoma is molten
It include precursor molecule and organic solvent in liquid, the precursor molecule is Porphyrin Molecule or Phthalocyanine, is wrapped in the precursor molecule
Include crosslinked group.
9. cross-linking hole transport layer material according to claim 8, which is characterized in that the OLED device is inversion type
OLED device, the OLED display panel further include pixel defining layer, are set on the underlay substrate, and define pixel region
Domain；The OLED device corresponds to the pixel region setting.
10. cross-linking hole transport layer material according to claim 8, which is characterized in that the organic solvent includes virtue
At least one of fragrant hydro carbons, ethers, esters solvent；It further include bridged group, substituent group, the bridge in the precursor molecule
Even group includes trianilino group or carbazoles group, and the substituent group includes alkyl or tert-butyl, the crosslinked group packet
It includes to styrene group.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910145196.6A CN109873086A (en) | 2019-02-27 | 2019-02-27 | A kind of cross-linking hole transport layer material and preparation method thereof |
| PCT/CN2019/079065 WO2020172930A1 (en) | 2019-02-27 | 2019-03-21 | Crosslinkable hole transport layer material and preparation method therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910145196.6A CN109873086A (en) | 2019-02-27 | 2019-02-27 | A kind of cross-linking hole transport layer material and preparation method thereof |
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| WO (1) | WO2020172930A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111116946A (en) * | 2019-12-31 | 2020-05-08 | 深圳市华星光电半导体显示技术有限公司 | Hole transport material, display panel and manufacturing method thereof |
| CN111416050A (en) * | 2020-04-16 | 2020-07-14 | 苏州欧谱科显示科技有限公司 | Hole transport material and application thereof |
| CN113745441A (en) * | 2021-08-20 | 2021-12-03 | 深圳市华星光电半导体显示技术有限公司 | Display panel and preparation method thereof |
| WO2022032757A1 (en) * | 2020-08-11 | 2022-02-17 | Tcl华星光电技术有限公司 | Three-dimensional dye, method for preparing three-dimensional dye, and photoresist mixture |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111116946A (en) * | 2019-12-31 | 2020-05-08 | 深圳市华星光电半导体显示技术有限公司 | Hole transport material, display panel and manufacturing method thereof |
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| CN111416050A (en) * | 2020-04-16 | 2020-07-14 | 苏州欧谱科显示科技有限公司 | Hole transport material and application thereof |
| CN111416050B (en) * | 2020-04-16 | 2022-08-05 | 苏州欧谱科显示科技有限公司 | Hole transport material and application thereof |
| WO2022032757A1 (en) * | 2020-08-11 | 2022-02-17 | Tcl华星光电技术有限公司 | Three-dimensional dye, method for preparing three-dimensional dye, and photoresist mixture |
| CN113745441A (en) * | 2021-08-20 | 2021-12-03 | 深圳市华星光电半导体显示技术有限公司 | Display panel and preparation method thereof |
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| Publication number | Publication date |
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| WO2020172930A1 (en) | 2020-09-03 |
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Application publication date: 20190611 |