CN114068825B - Organic electroluminescent device and display device having multi-hole transport channel material - Google Patents

Organic electroluminescent device and display device having multi-hole transport channel material Download PDF

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CN114068825B
CN114068825B CN202010746922.2A CN202010746922A CN114068825B CN 114068825 B CN114068825 B CN 114068825B CN 202010746922 A CN202010746922 A CN 202010746922A CN 114068825 B CN114068825 B CN 114068825B
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organic electroluminescent
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CN114068825A (en
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王芳
李崇
张兆超
崔明
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Jiangsu Sunera Technology Co Ltd
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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
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Abstract

The invention relates to an organic electroluminescent device, which comprises a cathode and an anode which are opposite to each other, and a hole injection conductive film layer combination, a light emitting film layer combination and an electron injection film layer combination which are sequentially arranged between the anode and the cathode, wherein the hole injection conductive film layer combination comprises at least one multi-hole transport channel material as described in the specification, wherein the molecular structure of the multi-hole transport channel material comprises more than two hole transport channels as described in the specification, and the difference of the front line track delocalization indexes of the two hole transport channels is more than or equal to 2%. The invention also relates to a full color display device comprising the organic electroluminescent device of the invention.

Description

Organic electroluminescent device and display device having multi-hole transport channel material
Technical Field
The present invention relates to the field of semiconductor technology, and more particularly, to an organic electroluminescent device having a multi-hole transport channel material, and a full color display apparatus including the same.
Background
Carriers (holes and electrons) in an organic electroluminescent device (OLED) are respectively injected into the device by two electrodes of the device under the drive of an electric field, and meet and recombine and emit light in an organic light-emitting layer. High-performance organic electroluminescent devices require various organic functional materials to have good photoelectric properties. For example, a charge transport material is required to have good carrier mobility. The injection and transmission characteristics of a hole injection layer and a hole transmission layer used in the existing organic electroluminescent device are relatively weak, and the hole injection and transmission rates are not matched with the electron injection and transmission rates, so that the offset of a composite area is larger, and the stability of the device is not facilitated. In addition, reasonable energy level matching of the hole injection layer material and the hole transport layer material is an important factor for improving the efficiency and the service life of the device, so that improving the injection and the transport of holes has important significance for reducing the driving voltage of the device and improving the luminous efficiency and the service life of the device.
Blue organic electroluminescent devices are always soft ribs in full-color OLED development, so that the efficiency, service life and other performances of blue light devices are not fully improved until now, and therefore, how to improve the performances of the devices is still a critical problem and challenge in the field. Since the blue light host materials currently used in the market are mostly electron-biased host materials, the hole transport materials are required to have excellent hole transport properties in order to adjust the carrier balance of the light emitting layer. The better the hole injection and transmission, the more the adjusting composite area is deviated to the side far away from the electron blocking layer, so that the light is emitted far away from the interface, the performance of the device is improved, and the service life of the device is prolonged. Therefore, how to improve the transport characteristics of the hole transport material has been an important research topic.
The hole transport material has a relatively thick film thickness, and therefore, heat resistance and amorphism of the material have a critical influence on the lifetime of the device. The material with poor heat resistance is easy to decompose in the evaporation process, pollutes the evaporation cavity and damages the service life of the device; the material with poor film phase stability can be crystallized in the use process of the device, and the service life of the device is reduced. Therefore, the hole transport material is required to have high film phase stability and decomposition temperature during use.
Disclosure of Invention
In order to solve the above problems, the present inventors have found that, in a hole injection conductive film layer constituting an organic electroluminescent device, if a multi-hole transport channel material is provided, hole injection and transport effects can be effectively improved, which is more conducive to reducing interface barriers between different functional layers and improving interface stability, and thus is conducive to improving the overall performance of the organic electroluminescent device including luminous efficiency, driving voltage and driving life.
A multiple hole transport channel material refers to a material having more than two hole conducting channels, where one channel contains only one nitrogen atom and the other channel contains two or more nitrogen atoms. The inventors have found that the hole transport rate is closely related to the molecular front-line orbital distribution. The greater the difference in the extent of front track delocalization, the greater the difference in energy, the less likely hole flow will occur. When the degree of dislocation of the front line track is greater than or equal to 2%, the flow of holes between different tracks hardly occurs, and thus a plurality of hole conduction channels are generated. Because the material contains a plurality of hole conduction channels, the hole mobility of the material is greatly improved, and the device performance is improved.
Due to the existence of multiple hole transmission channels, holes can be effectively transmitted, the charge is effectively prevented from accumulating in molecules to damage the stability of materials, the interface stability and the film phase stability are improved, and the stability of devices is further improved.
It is therefore an object of the present invention to provide a high performance organic electroluminescent device. The injection and conduction of holes in the organic electroluminescent device are more beneficial to the tunneling mode because of the existence of the multi-hole transmission channel material, so that the injection conduction efficiency of the holes is easily improved, and the effect of low-voltage driving is achieved; meanwhile, holes are easier to conduct to the light-emitting layer, so that balance of carriers is facilitated, and improvement of device performance is facilitated.
This object is achieved by an organic electroluminescent device comprising: a cathode and an anode opposite to each other, a hole injection conductive film layer combination, a light emitting film layer combination, and an electron injection film layer combination sequentially disposed between the anode and the cathode,
wherein the hole injection conductive film layer composition comprises at least one multi-hole transport channel material having a triazo structure characteristic and containing an aromatic amine group or carbazole group as shown in formula (A) or formula (B),
The molecular structural formulas (A) and (B) of the multi-hole transport channel material respectively comprise more than two hole transport channels, the hole transport channels are composed of hole transport fragments shown in the formula (1) or the formula (2),
the difference between the foreline orbital delocalization index of the hole conduction fragment shown in the formula (1) and the foreline orbital delocalization index of the hole conduction fragment shown in the formula (2) is more than or equal to 2%;
wherein, the liquid crystal display device comprises a liquid crystal display device,
R、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 respectively and independently represented as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
R 0 represented by H, substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted C 5 -C 30 Heteroaryl;
A. b is independently represented by a hydrogen atom, C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl, alternatively represented as a fused ring with two adjacent carbon atoms on the benzene ring;
l represents a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 5 -C 30 Heteroarylene;
l1 is represented by substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 5 -C 30 Heteroarylene;
wherein in the case of substitution, the substituents are independently selected from deuterium atoms, halogen atoms, C 1 -C 10 Alkoxy, adamantyl, cyano, C 1 -C 10 Alkyl, C 3 -C 20 Cycloalkyl, C 6 -C 30 Aryl, C containing one or more hetero atoms independently of one another selected from N, S and O 5-30 Heteroaryl, or a combination thereof.
It is also an object of the present invention to provide a full-color display device comprising three pixels of red, green and blue, the full-color display device comprising the organic electroluminescent device of the present invention.
The invention has the beneficial effects that:
the invention uses multi-hole transmission channel material in the hole injection conductive film layer, thereby having more than two hole transmission channels. Different hole conduction channels allow holes to pass along different transport channels due to the difference in molecular front orbitals. Holes can be jointly transmitted on the channels respectively in the injection and conduction processes, so that the injection and transmission efficiency of the holes is greatly improved. The higher hole injection characteristic and hole transmission rate are beneficial to deviating the recombination region from one side of hole transmission, effectively prevent excitons from accumulating at the interface, reduce the degradation of the device and further improve the service life of the device.
Due to the existence of multiple hole transmission channels, holes can be effectively transmitted, the charge is effectively prevented from accumulating in molecules to damage the stability of materials, the interface stability and the film phase stability are improved, and the stability of devices is further improved.
In the hole transport region, holes form electron exchange in different conduction channels and conduct along various hole channels, so that injection and transport effects of holes are improved, and an organic electroluminescent device with high efficiency and low voltage can be realized.
Drawings
Fig. 1 schematically illustrates a cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
1 represents an anode; 10 denotes a hole injection conductive film layer composition, 2 denotes a hole injection layer, 3 denotes a hole transport layer, and 4 denotes an electron blocking layer; 5 represents a luminescent film layer combination; 20 denotes an electron injection film layer composition, 6 denotes an electron transport layer, and 7 denotes an electron injection layer; 8 is denoted as cathode; 9 denotes a cover layer; 30 denotes an organic light emitting diode.
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are merely illustrative, the invention is not limited thereto and the invention is defined by the scope of the claims.
In the present invention, unless otherwise indicated, all operations are carried out at room temperature under normal pressure.
In the present invention, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule unless otherwise specified. Further, reference in the present specification to "difference in HOMO energy levels" and "difference in LUMO energy levels" means a difference in absolute values of each energy value. Furthermore, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between energy levels is also a comparison of the magnitudes of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level, the lower the energy of the energy level.
In the present invention, when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate or intervening layers may also be present. Further, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers or one or more intervening layers may also be present. Like numbers refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, words of "upper", "lower", "top" and "bottom", etc., which are used to indicate orientations, indicate only orientations in a certain specific state, and do not mean that the relevant structure can only exist in the orientations; conversely, if the structure can be repositioned, for example inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of an electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is farther from the substrate is the "top" side.
In the present specification, "C 6 -C 30 Aryl "refers to a fully unsaturated monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing a pair of adjacent carbon atoms) system having from 6 to 30 ring carbon atoms.
In the present specification, the terms“C 5 -C 30 Heteroaryl "refers to a fully unsaturated monocyclic, polycyclic or fused polycyclic ring system having 5 to 30 ring carbon atoms and containing at least one heteroatom selected from N, O and S. When the heteroaryl group is a fused polycyclic ring, each or all of the rings of the heteroaryl group may contain at least one heteroatom.
More specifically, substituted or unsubstituted C 6 -C 30 Aryl and/or substituted or unsubstituted C 5 -C 30 Heteroaryl means a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fused tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-biphenylyl group, a substituted or unsubstituted m-biphenylyl group, a substituted or unsubstituted p-biphenylyl groupA substituted or unsubstituted biphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted porphyrazinyl, substituted or unsubstituted benzoxazinyl The fluorene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazole group, a combination thereof, or a condensed ring of the combination of the foregoing groups, but is not limited thereto.
In the present specification, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 5 -C 30 Heteroarylene means a substituted or unsubstituted C as defined above and having two linking groups 6 -C 30 Aryl or substituted or unsubstituted C 5 -C 30 Heteroaryl groups, e.g. substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fused tetraphenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted phenyleneA substituted or unsubstituted biphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted indenylene, a substituted or unsubstituted furanylene, a substituted or unsubstituted thiophenylene, a substituted or unsubstituted pyrrolylene, a substituted or unsubstituted pyrazolylene, a substituted or unsubstituted imidazolylene, a substituted or unsubstituted triazolylene, a substituted or unsubstituted oxazolylene, a substituted or unsubstituted thiazolylene, a substituted or unsubstituted oxadiazolylene, a substituted or unsubstituted thiadiazolylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted triazinylene, substituted or unsubstituted benzofuranylene, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolylene, substituted or unsubstituted indolylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazolylene, substituted or unsubstituted benzoxazolyl Unsubstituted benzothiazinylene, substituted or unsubstituted acriylene, substituted or unsubstituted porphazinylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene, combinations thereof, or fused rings of combinations of the foregoing, but are not limited thereto.
C of the invention 1 -C 10 Alkyl refers to methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, sec-butyl, pentyl, isopentyl, octyl, heptyl, or the like, but is not limited thereto.
The halogen atom in the present invention means a chlorine atom, a fluorine atom, a bromine atom, or the like, but is not limited thereto.
C of the invention 1 -C 10 Alkoxy refers to methoxy, ethoxy, or isopropoxy, etc., but is not limited thereto.
C of the invention 3 -C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as ring-forming atoms. In this context, preference is given to using C 4 -C 9 Cycloalkyl groups, more preferably C 5 -C 8 Cycloalkyl radicals, particularly preferably C 5 -C 7 Cycloalkyl groups. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. C as used herein 3 -C 10 Cycloalkylene means and C 3 -C 10 Cycloalkyl groups have divalent groups of the same structure.
In this specification, the hole feature refers to a feature that can supply electrons when an electric field is applied and is attributed to a conductive feature according to the Highest Occupied Molecular Orbital (HOMO) level, and holes formed in the anode are easily injected into and transported in the light emitting layer.
In this specification, the electron feature refers to a feature that can accept electrons when an electric field is applied and is attributed to a conductive feature according to the Lowest Unoccupied Molecular Orbital (LUMO) level, electrons formed in the cathode are easily injected into and transported in the light emitting layer.
Organic electroluminescent device
The present invention provides an organic electroluminescent device having improved luminous efficiency and lifetime, comprising: a cathode and an anode opposite to each other, a hole injection conductive film layer combination, a light emitting film layer combination, and an electron injection film layer combination sequentially disposed between the anode and the cathode,
wherein the hole injection conductive film layer composition comprises at least one multi-hole transport channel material having a triazo structure characteristic and containing an aromatic amine group or carbazole group as shown in formula (A) or formula (B),
the molecular structural formulas (A) and (B) of the multi-hole transport channel material respectively comprise more than two hole transport channels, the hole transport channels are composed of hole transport fragments shown in the formula (1) or the formula (2),
The difference between the foreline orbital delocalization index of the hole conduction fragment shown in the formula (1) and the foreline orbital delocalization index of the hole conduction fragment shown in the formula (2) is more than or equal to 2%;
wherein, the liquid crystal display device comprises a liquid crystal display device,
R、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 respectively and independently represented as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
R 0 represented by H, substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted C 5 -C 30 Heteroaryl;
A. b is independently represented by a hydrogen atom, C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl groups, alternatively denoted as being bound to benzene ringsIs fused to form a ring;
l represents a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 5 -C 30 Heteroarylene;
l1 is represented by substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 5 -C 30 Heteroarylene;
wherein in the case of substitution, the substituents are independently selected from deuterium atoms, halogen atoms, C 1 -C 10 Alkoxy, adamantyl, cyano, C 1 -C 10 Alkyl, C 3 -C 20 Cycloalkyl, C 6 -C 30 Aryl, C containing one or more hetero atoms independently of one another selected from N, S and O 5-30 Heteroaryl, or a combination thereof.
In a preferred embodiment of the present invention, the difference in the front-line orbital delocalization index of the hole-conducting fragment represented by formula (1) and the hole-conducting fragment represented by formula (2) is 3% or more, preferably 20% or less, preferably between 5 and 15%, more preferably between 8 and 12%.
Preferably, the multiple hole transport channel material is a compound represented by formula (A1):
therein, L, R 4 、R 5 、R 6 、R 7 Each represents a group as defined above;
n is represented by the number 1, 2 or 3.
Preferably, the multiple hole transport channel material is a compound represented by formula (A2):
therein, L, R 4 、R 5 、R 6 、R 7 Each represents a radical as defined aboveA bolus;
n represents the number 1, 2 or 3;
a is C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl groups, or as fused rings with two adjacent carbon atoms in the carbazole group.
Preferably, the multiple hole transport channel material is a compound represented by formula (A3):
therein, L, R 0 、R 4 、R 5 、R 6 、R 7 Each represents a group as defined above;
n is represented by the number 1, 2 or 3.
Preferably, the multiple hole transport channel material is a compound represented by formula (A4):
therein, L, R 0 、R 4 、R 6 、R 7 Each represents a group as defined above;
Ar 1 represented by a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group;
ar represents phenyl, naphthyl, biphenyl, terphenyl or dibenzofuranyl;
n is represented by the number 1, 2 or 3.
Preferably, the multi-hole transport channel material has a structure represented by formula (B1);
therein, L, L 1 、R、R 2 、R 1 、R 4 Each represents a group as defined above.
In a preferred embodiment of the present invention, the multiple hole transport channel material may be selected from any one of the following compounds:
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in a more preferred embodiment of the present invention, the multiple hole transport channel material may be selected from any one of the following compounds:
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the multi-hole transmission channel material can obviously improve the injection and transmission rate of holes. Herein, hole-conducting groups that may be cited include carbazole groups, anilino groups, carbazolo ring groups, and the like. In order to realize multi-level hole conduction based on the principle of the present invention, the hole conduction group constituting the hole transport material must not be one, but a plurality of hole type groups exist, such as the molecular structural characteristics of one aniline and one carbazole, the molecular structural characteristics of three anilines, the molecular structural characteristics of two anilines and one carbazole, and the like.
The hole transport material is characterized in that more than two front line orbit delocalization index levels are arranged in the hole transport fragments forming the hole transport material, and the difference between the two front line orbit delocalization index levels is more than or equal to 2%.
For the purpose of the invention, the method for judging whether a molecule has a plurality of hole conduction channels is to disassemble the molecular structure at different hole conduction fragments, wherein the disassembly principle is that one fragment contains one nitrogen atom and the other fragment contains two nitrogen atoms, the foreline orbit delocalization index of each disassembled molecular fragment is calculated, and the difference of the hole conduction channels of the disassembled material is judged, so that the quality and physical property quality of the molecule are judged. An exemplary manner of disassembling the molecule is as follows:
Can be disassembled into->Two structures;
can be disassembled into->Two structures;
can be disassembled into->Two structures.
The front orbit delocalization index of the disassembled molecular fragments can be calculated using the beijing family sound natural research center software multisfn Manual, version 3.7 (dev). Specifically, after the multi-hole transport channel material is disassembled into the hole conducting segment of formula (1) and the hole conducting segment of formula (2), the front line orbital delocalization index of each hole conducting segment can be calculated through the software simulation, and the difference value of the front line orbital delocalization indexes of the hole conducting segments is calculated.
The invention does not negate the substrate collocation principle of the traditional hole materials, but further superposes on the basis of physical parameters of traditional material screening, namely, the effect of HOMO energy level, hole mobility, film phase stability, heat-resistant stability of the materials and the like on the hole injection efficiency of the organic electroluminescent device is admitted. On the basis, the material screening conditions are further increased, and further, the selection accuracy of the materials for preparing the high-performance organic electroluminescent device is improved by selecting more excellent organic electroluminescent materials to be used for matching devices.
The organic electroluminescent device of the present invention may be a bottom-emission organic electroluminescent device, a top-emission organic electroluminescent device, and a stacked organic electroluminescent device, and is not particularly limited.
In the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices may also be used. Examples thereof are transparent substrates such as glass or transparent plastic substrates; an opaque substrate such as a silicon substrate; a flexible Polyimide (PI) film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water repellency. The use direction of the substrate is different according to the property of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
Anode
Preferably, the anode may be formed on the substrate. In the present invention, the anode and the cathode are opposite to each other. The anode may be made of a conductor, such as a metal, metal oxide, and/or conductive polymer, having a higher work function to aid in hole injection. The anode may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, silver, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals with oxides, such as ZnO with Al or SnO 2 Sb, or ITO and Ag; conductive polymers such as poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene) (PEDOT), polypyrrole, and polyaniline, but are not limited thereto. The thickness of the anode depends on the material used, and is generally 50 to 500nm, preferably 70 to 300nm, and more preferably 100 to 200nm.
Cathode electrode
The cathode may be made of a conductor with a lower work function to aid in electron injection and may be, for example, a metal, metal oxide, and/or conductive polymer. The cathode may be, for example, a metal or alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, and barium; multilayer structural materials, such as LiF/Al, li 2 O/Al, liF/Ca and BaF 2 /Ca, but is not limited thereto. The thickness of the cathode is generally 10-50nm, preferably 15-20nm, depending on the material used.
Light-emitting film layer composition
In the present invention, the light emitting film layer combination may be disposed between the anode and the cathode, and may include at least one host material and at least one guest material. As the host material and the guest material of the light-emitting film layer of the organic electroluminescent device of the present invention, materials for light-emitting layers of organic electroluminescent devices known in the art can be used. The host material may be, for example, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or 4,4' -bis (9-Carbazolyl) Biphenyl (CBP). Preferably, the host material may comprise anthracene groups. The guest material may be, for example, quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives or aminostyrene derivatives.
In a preferred embodiment of the present invention, one or two host material compounds are contained in the luminescent film layer.
In a preferred embodiment of the present invention, two host material compounds are included in the light emitting film layer, and the two host material compounds form an exciplex.
In a preferred embodiment of the present invention, the host material of the luminescent film layer used is selected from one or more of the following compounds BH-1 to BH-24:
in the present invention, the light emitting film layer may contain a phosphorescent or fluorescent guest material to improve fluorescence or phosphorescence characteristics of the organic electroluminescent device. Specific examples of phosphorescent guest materials include metal complexes of iridium, platinum, and the like. For example, ir (ppy) may be used 3 [ fac-tris (2-phenylpyridine) iridium]Green phosphor materials, blue phosphor materials such as FIrpic and FIr6, and red phosphor materials such as Btp2Ir (acac). For the fluorescent guest material, those generally used in the art can be used. In a preferred embodiment of the present invention, the guest material of the light-emitting film layer used is selected from one of the following compounds BD-1 to BD-23:
in the light-emitting film layer of the present invention, the ratio of host material to guest material used is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
In the light emitting film layer of the present invention, the host material may also be mixed with a small amount of a dopant, which may be an organic compound or a metal complex, such as Al that emits fluorescence by singlet excitation, to produce light emission; or a material such as a metal complex that emits light by being excited into a triplet state or more by a multiple state. The dopant may be, for example, an inorganic compound, an organic compound, or an organic/inorganic compound, and one or more kinds thereof may be used.
Examples of dopants may be organometallic compounds comprising Ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd or combinations thereof. The dopant may be, for example, a compound represented by the following formula (Z), but is not limited thereto:
L 2 MX type (Z)
Wherein, the liquid crystal display device comprises a liquid crystal display device,
m is a metal, and is a metal,
l is the same as or different from X and is a ligand forming a complex with M.
In one embodiment of the invention, M may be, for example, ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd or a combination thereof, and L and X may be, for example, bidentate ligands.
The thickness of the light emitting film layer of the present invention may be 10 to 50nm, preferably 15 to 30nm, but the thickness is not limited to this range.
Hole injection conductive film layer composition
In the organic electroluminescent device of the present invention, a hole injection conductive film layer composition is provided between the anode and the light emitting film layer composition, which includes a hole injection layer, a hole transport layer, and an electron blocking layer. In one embodiment of the present invention, the hole injection layer and the hole transport layer comprise the same multi-hole transport channel material described above, and wherein the hole injection layer is a mixed film of the multi-hole transport channel material and the P-type dopant material.
In order to enable holes to be smoothly injected from the anode to the organic film layer, the HOMO level of the host organic material (i.e., the multi-hole transport channel material of the present invention) used for the hole injection layer (also referred to as the anode interface buffer layer) that conducts holes must have a certain characteristic with the P-type doping material, so that it is expected that the occurrence of a charge transfer state between the host material and the doping material, and ohmic contact between the hole injection layer and the anode, and efficient injection of holes from the electrode to the hole injection layer, are achieved. This feature is summarized as: the difference between the HOMO energy level of the host material and the LUMO energy level of the P-type doped material is less than or equal to 0.4eV. Therefore, for hole host materials with different HOMO energy levels, different P-type doping materials are required to be selected to be matched with the hole host materials, so that ohmic contact of an interface can be realized, and the hole injection effect is improved. Preferably, the P-type dopant material is a compound having charge conductivity selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinone dimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4"- ((1 e,1' e,1" e) -cyclopropane-1, 2, 3-trimethylenetris (cyanoformylidene)) tris (2, 3,5, 6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
In a preferred embodiment of the invention, the P-type doping material used is selected from any of the following compounds HI-1 to HI-10:
in one embodiment of the invention, the ratio of hole transporting host material to P-type dopant material used is 99:1 to 95:5, preferably 99:1 to 97:3, on a mass basis.
In the organic electroluminescent device of the present invention, the hole transport layer may be disposed on the hole injection layer, and it includes the same multi-hole transport channel material as the hole injection layer.
In the organic electroluminescent device of the present invention, an electron blocking layer may be disposed between the hole transport layer and the light emitting layer, and particularly contact the light emitting layer. The electron blocking layer is disposed to contact the light emitting layer, and thus, hole transfer at the interface of the light emitting layer and the hole transporting layer can be precisely controlled. The electron blocking layer may comprise structural fragments having different energy levels, and the difference in energy level between the structural fragments is between 0.02 and 0.5 eV.
In one embodiment of the invention, the HOMO level of the electron-blocking layer is between 5.50 and 5.85eV, preferably between 5.55 and 5.75eV, more preferably between 5.60 and 5.75 eV.
In a preferred embodiment of the invention, the triplet energy level (T1) of the electron blocking layer is ≡2.4eV. In another embodiment of the invention, the electron blocking layer has a bandgap width (Eg). Gtoreq.3.0 eV.
In one embodiment of the invention, the difference in HOMO levels of the electron blocking layer and the hole transport layer is less than 0.3eV.
In the organic electroluminescent device of the present invention, the electron blocking layer comprises a carbazole derivative represented by general formula (E):
wherein the method comprises the steps of
Ar 1 、Ar 2 Each independently represents substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
Ar 3 、Ar 4 each independently represented as a hydrogen atom, a substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
C. d is independently represented by a hydrogen atom, C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl, or represented as a fused ring with two adjacent carbon atoms in the carbazole group;
m represents the number 0, 1, 2 or 3;
wherein in the case of substitution, the substituents are independently selected from deuterium atoms, halogen atoms, C 1 -C 10 Alkoxy, adamantyl, cyano, C 1 -C 10 Alkyl, C 3 -C 20 Cycloalkyl, C 6 -C 30 Aryl, C containing one or more heteroatoms independently of one another selected from N, O and S 5 -C 30 Heteroaryl, or a combination thereof.
Preferably, the electron blocking layer contains a carbazole derivative represented by general formula (E1):
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 、Ar 2 each independently represents substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
Ar 3 、Ar 4 each independently represented as a hydrogen atom, a substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl, and Ar 3 、Ar 4 At least one of which is not represented as a hydrogen atom;
m represents the number 0, 1, 2 or 3.
Preferably, the electron blocking layer contains a carbazole derivative represented by general formula (E2):
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 、Ar 2 representing fetch independently of each otherSubstituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
Ar 3 、Ar 4 each independently represented as a hydrogen atom, a substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl, and Ar 3 、Ar 4 At least one of which is not represented as a hydrogen atom;
C. d is independently represented by a hydrogen atom, C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl, or represented as a fused ring with two adjacent carbon atoms in the carbazole group, and at least one of said C, D is not represented as a hydrogen atom;
m represents the number 0, 1, 2 or 3.
In a preferred embodiment of the present invention, the electron blocking layer comprises any one of the following compounds selected from:
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in a more preferred embodiment of the present invention, the electron blocking layer comprises any one of the following compounds selected from:
the thickness of the hole injection layer of the present invention may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
The thickness of the hole transport layer of the present invention may be 80 to 200nm, preferably 100 to 150nm, but the thickness is not limited to this range.
The thickness of the electron blocking layer of the present invention may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Electron injection film layer composition
In the organic electroluminescent device of the present invention, an electron injection film layer composition is disposed between the light emitting film layer composition and the cathode, which includes an electron transport layer and an electron injection layer, but is not limited thereto.
The electron transport layer may be disposed over the light emitting film layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials for organic electroluminescent devices known in the art, for example, alq 3 Metal complexes of hydroxyquinoline derivatives represented by BAlq and LiQ, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS No.: 1459162-51-6), and 2- (4- (9, 10-bis (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d ]]Imidazole derivatives such as imidazole (CAS number: 561064-11-7, commonly known as LG 201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, and the like. The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm and more preferably 25 to 45nm, but the thickness is not limited to this range.
The electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal material. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
Cover layer
In order to improve the light-emitting efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be further added to the cathode of the device. According to the optical absorption and refraction principles, the higher the refractive index of the CPL cover layer material is, the better the CPL cover layer material is, and the smaller the light absorption coefficient is, the better the CPL cover layer material is. Any material known in the art may be used as the CPL layer material, such as Alq3, or N4, N4' -diphenyl-N4, N4' -bis (9-phenyl-3-carbazolyl) biphenyl-4, 4' -diamine. The CPL coating typically has a thickness of 5-300nm, preferably 20-100nm and more preferably 40-80nm.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
Hereinafter, an organic electroluminescent device according to an embodiment of the present invention is described.
The organic electroluminescent device may be any element that converts electric energy into light energy or converts light energy into electric energy without particular limitation, and may be, for example, an organic electroluminescent device, an organic light emitting diode, an organic solar cell, and an organic photoconductor. Herein, the organic light emitting diode is described as one example of an organic electroluminescent device (but the present invention is not limited thereto), and may be applied to other organic electroluminescent devices in the same manner.
In the drawings, the thickness of layers, films, substrates, regions, etc. are exaggerated for clarity. Like numbers refer to like elements throughout. It will be understood that when an element such as a layer, film, region or substrate is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
Fig. 1 is a schematic cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
Referring to fig. 1, an organic light emitting diode 30 according to an embodiment of the present invention includes an anode 1 and a cathode 8 opposite to each other, a hole injection conductive film layer composition 10, a light emitting film layer composition 5, and an electron injection film layer composition 20 sequentially disposed between the anode 1 and the cathode 8, and a capping layer 9 disposed over the cathode, wherein the hole injection conductive film layer composition 10 includes a hole injection layer 2, a hole transport layer 3, and an electron blocking layer 4, and the electron injection film layer composition 20 includes an electron transport layer 6 and an electron injection layer 7.
The invention also relates to a method of manufacturing an organic electroluminescent device comprising sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, the respective layers are preferably formed by a vacuum vapor deposition method. The individual process conditions in the vacuum evaporation process can be routinely selected by those skilled in the art according to the actual needs.
The material for forming each layer according to the present application may be used as a single layer by forming a film alone, or may be used as a single layer by forming a film after mixing with another material, or may be a laminated structure between layers formed by forming a film alone, a laminated structure between layers formed by mixing, or a laminated structure between layers formed by forming a film alone and layers formed by mixing.
The application also relates to a full-color display device, in particular a flat panel display device, comprising the organic electroluminescent device of the application with three pixels of red, green and blue. The display device may further include at least one thin film transistor. The thin film transistor may include a gate electrode, source and drain electrodes, a gate insulating layer, and an active layer, wherein one of the source and drain electrodes may be electrically connected to an anode of the organic electroluminescent device. The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, or an oxide semiconductor, but is not limited thereto.
Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used in a generic and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art as the present disclosure proceeds, features, characteristics, and/or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics, and/or elements described in connection with other embodiments unless specifically indicated. Accordingly, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the application.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
Examples
Unless otherwise indicated, the various materials used in the following examples and comparative examples are commercially available or may be obtained by methods known to those skilled in the art.
Preparation of Compounds of formula (A)
Example 1: synthesis of Compound 141
250ml three-necked flask was charged with 0.02mol of raw material A-1,0.012mol of raw material B-1,0.03mol of potassium tert-butoxide, 1X 10 under an atmosphere of nitrogen -4 mol Pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heating and refluxing for 12 hours, sampling the spot plate, and completely reacting; naturally cooling, filtering, steaming the filtrate, and passing through a silica gel column (eluent is n-hexane: ethyl acetate=1:1 (volume ratio)) to obtain an intermediate A-1. Elemental analysis structure (molecular formula C) 22 H 16 BrN): theoretical value C,70.60; h,4.31; br,21.35; n,3.74; test value: c,70.64; h,4.32; br,21.37; n,3.75.MS (M/z) (m+): theoretical 373.05 and measured 373.41.
250ml three-necked flask was charged with 0.01mol of intermediate A-1,0.012mol of raw material C-1,0.03mol of potassium tert-butoxide, 1X 10 under an atmosphere of nitrogen -4 mol Pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heating and refluxing for 12 hours, sampling the spot plate, and completely reacting; naturally cooling, filtering, steaming the filtrate, and passing through a silica gel column (eluent is n-hexane: ethyl acetate=1:1 (volume ratio)) to obtain an intermediate B-1. Elemental analysis structure (molecular formula C) 40 H 27 BrN 2 ): theoretical value C,78.05; h,4.42; br,12.98; n,4.55; test value: c,78.03; h,4.43; br,12.97; n,4.57.MS (M/z) (m+): theoretical 614.14 and measured 614.27.
250ml three-necked flask was charged with 0.01mol of D-1,0.012mol of intermediate B-1,0.03mol of potassium tert-butoxide, 1X 10 under nitrogen atmosphere -4 mol Pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heating and refluxing for 12 hours, sampling the spot plate, and completely reacting; naturally cooling, filtering, steaming the filtrate, and passing through a silica gel column (eluent is n-hexane: ethyl acetate=1:1 (volume ratio)) to obtain the target compound 141. Elemental analysis structure (molecular formula C) 52 H 37 N 3 ): theoretical C,88.73; h,5.30; n,5.97; test value: c,88.76; h,5.32; n,5.97.MS (m-z) (m+): theoretical 703.20 and measured 703.47.
Example 2: synthesis of Compound 227
250ml three-necked flask was charged with 0.02mol of raw material A-1,0.012mol of raw material B-1,0.03mol of potassium tert-butoxide, 1X 10 under an atmosphere of nitrogen -4 mol Pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heating and refluxing for 12 hours, sampling the spot plate, and completely reacting; naturally cooling, filtering, steaming the filtrate, and passing through a silica gel column (eluent is n-hexane: ethyl acetate=1:1 (volume ratio)) to obtain an intermediate A-1. Elemental analysis structure (molecular formula C) 22 H 16 BrN): theoretical value C,70.60; h,4.31; br,21.35; n,3.74; test value: c,70.64; h,4.32; br,21.37; n,3.75.MS (M/z) (m+): theoretical 373.05 and measured 373.41.
In a 250ml three-necked flask, under the protection of nitrogen, 0.02mol of raw material C-2,0.012mol of intermediate A-1,0.02mol of sodium carbonate and 150ml of toluene are added, stirred and mixed, and then 1X 10 is added -4 mol Pd(pph 3 ) 4 Heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a spot plate, and displaying that no brominated substance remains and the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation (-0.09 MPa,85 ℃) on the filtrate, and passing through a neutral silica gel column (eluent is n-hexane: ethyl acetate=1:1 (volume ratio)) to obtain an intermediate B-2. Elemental analysis structure (molecular formula C) 40 H 31 BN 2 O 2 ): theoretical value C,81.48; h,5.36; b,1.86; n,4.81; test value: c,81.49; h,5.35; b,1.84; n,4.85.MS (M/z) (m+): theoretical 582.25 and measured 582.37.
In a 250ml three-necked flask, under the protection of nitrogen, 0.01mol of raw material D-2,0.012mol of intermediate B-2,0.02mol of sodium carbonate and 150ml of toluene were added and mixed with stirring, and then 1X 10 was added -4 mol Pd(pph 3 ) 4 Heating to 105 ℃, refluxing and reacting for 24 hours, sampling the spot plate, and displaying no bromideThe rest, the reaction is complete; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation (-0.09 MPa,85 ℃) on the filtrate, and passing through a neutral silica gel column (eluent is n-hexane: ethyl acetate=1:1 (volume ratio)) to obtain a target compound 227. Elemental analysis structure (molecular formula C) 64 H 47 N 3 ): theoretical value C,89.58; h,5.52; n,4.90; test value: c,89.55; h,5.54; n,4.91.MS (M/z) (m+): theoretical 857.38 and measured 857.41.
The following compounds (starting materials used were all supplied from medium energy saving Mo Run) were prepared in the same manner as in example 1 or example 2, and the synthetic starting materials are shown in the following table 1. The synthesis of the electron blocking layer material used in the present invention is described in patent CN 110577511a, the raw materials used are all provided by the intermediate energy saving Mo Run.
TABLE 1
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Preparation of Compounds of formula (E)
Synthesis of Compound D1
250ml three-necked flask was charged with 0.01mol of P-1,0.012mol of Q-1,0.03mol of potassium tert-butoxide, 1X 10 under nitrogen -4 molPd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heated and refluxed for 12 hours, and a sampling spot plate shows that no iodo matter (raw material P-1) remains and the reaction is complete; naturally cooling, filtering, removing solvent by rotary evaporation, and filteringA sexual silica gel column (eluent is petroleum ether: dichloromethane=1:1 (volume ratio)) to obtain an intermediate R-1; elemental analysis structure (molecular formula C) 18 H 10 BrClO): theoretical value C,60.45; h,2.82; br,22.34; cl,9.91; test value C,60.43; h,2.81; br,22.36; cl,9.92.MS (M/z) (m+): theoretical 355.96 and measured 355.87.
250ml three-necked flask was charged with 0.01mol of R-1,0.012mol of intermediate Y-1,0.03mol of potassium tert-butoxide, 1X 10 under nitrogen atmosphere -4 molPd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heating and refluxing for 12 hours, sampling a spot plate, and displaying that no bromide (raw material R-1) remains and the reaction is complete; naturally cooling, filtering, steaming the filtrate to remove the solvent, and passing through a neutral silica gel column (eluent is petroleum ether: dichloromethane=1:1 (volume ratio)) to obtain an intermediate X-1; elemental analysis structure (molecular formula C) 30 H 18 ClNO): theoretical value C,81.17; h,4.09; n,3.16; cl 7.99; test value: c,81.18; h,4.07; n,3.14; cl 7.97.MS (M/z) (m+): theoretical 443.11 and measured 443.34.
In a 250ml three-necked flask, under the protection of nitrogen, 0.01mol of raw material X-1,0.012mol of intermediate Z-1,0.02mol of sodium carbonate and 150ml of toluene are added, stirred and mixed, and then 1X 10 is added -4 molPd(pph 3 ) 4 Heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a spot plate, and displaying that no chloro compound (raw material X-1) remains and the reaction is complete; naturally cooling to room temperature, filtering, and spin-evaporating the filtrate to remove the solvent, and passing through a neutral silica gel column (eluent is petroleum ether: dichloromethane=1:4 (volume ratio)) to obtain the target compound D1. Elemental analysis structure (molecular formula C) 54 H 38 ON 2 ): theoretical value C,88.98; h,4.98; n,3.84; test value: c,88.97; h,4.95; n,3.88.MS (M/z) (m+): theoretical 728.28 and measured 728.41.
Other compounds were synthesized with reference to D1, the starting materials for synthesis are shown in table a below;
table A
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Detection method
Glass transition temperature Tg: the temperature was increased at a rate of 10℃per minute as measured by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter).
HOMO energy level: the test was performed by an ionization energy measurement system (IPS 3) test as an atmospheric environment.
Eg energy level: a tangent line is drawn based on the ascending side of the ultraviolet spectrophotometry (UV absorption) base line and the first absorption peak of the material single film, and the value of the intersection point of the tangent line and the base line is calculated.
Front track delocalization index: simulation calculations were performed using the beijing family sound natural research center software multiswn Manual, version3.7 (dev).
Hole mobility: the material was fabricated as a single charge device, measured using space charge (induced) limited amperometry (SCLC).
Based on the design theory of the invention, the multi-hole transmission channel material can be disassembled into a molecular fragment 1 and a molecular fragment 2 with different hole transmission capacities, and the two fragments have a certain front line orbit delocalization index difference. The specific physical properties are shown in Table 2.
TABLE 2
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As can be seen from the data in table 2 above, the compounds selected using the mechanism of the present invention have two different molecular fragments, and the front orbital delocalization indices of the different molecular fragments have large differences, which results in the compounds of the present invention having multiple hole conduction channels, resulting in the compounds of the present invention having higher hole mobility. In addition, the compound of the invention also has proper HOMO energy level, higher hole mobility and wider band gap (Eg), and can realize an organic electroluminescent device with high efficiency, low voltage and long service life.
Preparation of organic electroluminescent device
The molecular structural formula of the materials involved in the following preparation process is shown as follows:
device preparation example 1
The organic electroluminescent device is prepared according to the following steps:
a) Using transparent glass as a substrate, washing an anode layer (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)) thereon, ultrasonically cleaning with deionized water, acetone and ethanol for 15 minutes, respectively, and then treating in a plasma cleaner for 2 minutes;
b) On the washed anode layer, hole transport material compound 30 and P-type doping material HI1 were placed in two vapor deposition sources, respectively, at a vacuum level of 1.0E -5 Controlling the evaporation rate of the compound 30 at Pa pressure to beThe evaporation rate of the P-type doped material is controlled to be +.>Co-steaming to form a hole injection layer with the thickness of 10nm;
c) Evaporating a hole transport layer on the hole injection layer in a vacuum evaporation mode, wherein the hole transport layer is made of a compound 30, and the thickness of the hole transport layer is 120nm;
d) Evaporating an electron blocking layer D1 on the hole transport layer by a vacuum evaporation method, wherein the thickness of the electron blocking layer D1 is 10nm;
e) Evaporating a luminescent layer material on the electron blocking layer by vacuum evaporation, wherein a host material is BH1, a guest material is BD1, the mass ratio is 97:3, and the thickness is 20nm;
f) Evaporating ET1 and Liq on the light-emitting layer in a vacuum evaporation mode, wherein the mass ratio of the ET1 to the Liq is 50:50, the thickness is 30nm, and the layer is used as an electron transport layer;
g) Evaporating LiF on the electron transport layer by vacuum evaporation, wherein the thickness of the LiF is 1nm, and the layer is an electron injection layer;
h) Vacuum evaporation of Mg over the electron injection layer: an Ag electrode layer with thickness of 16nm, which is a cathode layer;
i) CPL material CP-1 is vacuum evaporated on the cathode layer, and the thickness is 70nm.
Device preparation examples 2 to 50
The procedure of device preparation example 1 was followed, except that the organic materials in steps b), c), d) were replaced with the organic materials shown in table 3, respectively.
Device comparative example 1
The procedure of device preparation example 1 was followed, except that the hole transport material in steps b) and c) was replaced with HT1 and the organic material in step d) was replaced with EB1.
Device comparative example 2
The procedure of device preparation example 1 was followed, except that the hole transport material in steps b) and c) was replaced with HT2 and the organic material in step d) was replaced with EB1.
Device comparative examples 3 to 8
The procedure of device preparation example 1 was followed, except that the hole transport material in step b) and c) was replaced with HT2 and the organic material in the layer of step D) was replaced with D11, D28, D94, D125, D145, D151, respectively.
TABLE 3 Table 3
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After the OLED light-emitting device was fabricated as described above, the cathode and anode were connected using a well-known driving circuit, and various properties of the device were measured. The results of measuring the performance of the devices of examples 1 to 50 and comparative examples 1 to 8 are shown in Table 4.
TABLE 4 Table 4
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Note that: LT95 refers to the time taken for the device brightness to decay to 95% of the original brightness at a brightness of 1000 nits;
voltage, current efficiency and color coordinates were tested using an IVL (current-voltage-brightness) test system (fresco scientific instruments, su-state);
The life test system is an EAS-62C OLED life test system of japan systems research limited.
As can be seen from the results of table 4, the use of the multi-hole transport channel compound of the present invention as a hole injection and hole transport layer material effectively reduces the device voltage and increases the device lifetime due to the higher hole transport rate.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the described embodiments. On the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The foregoing embodiments are, therefore, to be construed as illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.
Symbol description
30: organic light emitting diode
1: anode
9: cover layer
8: cathode electrode
7: electron injection layer
6: electron transport layer
5: light-emitting film layer composition
3: hole transport layer
4: electron blocking layer
2: hole injection layer
10: hole injection conductive film layer composition
20: electron injection film layer composition

Claims (18)

1. An organic electroluminescent device, comprising: a cathode and an anode opposite to each other, a hole injection conductive film layer combination, a light emitting film layer combination, and an electron injection film layer combination sequentially disposed between the anode and the cathode,
Wherein the hole injection conductive film layer composition comprises at least one multi-hole transport channel material having a triazo structure characteristic and containing an aromatic amine group or carbazole group as shown in formula (A) or formula (B),
the molecular structural formulas (A) and (B) of the multi-hole transport channel material respectively comprise more than two hole transport channels, the hole transport channels are composed of hole transport fragments shown in the formula (1) or the formula (2),
the difference between the foreline orbital delocalization index of the hole conduction fragment shown in the formula (1) and the foreline orbital delocalization index of the hole conduction fragment shown in the formula (2) is more than or equal to 2%;
wherein the method comprises the steps of
R、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 Respectively and independently represented as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
R 0 is H, substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted C 5 -C 30 Heteroaryl;
A. b is independently represented by a hydrogen atom, C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl, alternatively represented as a fused ring with two adjacent carbon atoms on the benzene ring;
l represents a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 5 -C 30 Heteroarylene;
L 1 represented as substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 5 -C 30 Heteroarylene;
wherein in the case of substitution, the substituents are independently selected from deuterium atoms, halogen atoms, C 1 -C 10 Alkoxy, adamantyl, cyano, C 1 -C 10 Alkyl, C 3 -C 20 Cycloalkyl, C 6 -C 30 Aryl, C containing one or more heteroatoms independently of one another selected from N, O and S 5 -C 30 Heteroaryl, or a combination thereof.
2. The organic electroluminescent device according to claim 1, wherein a difference between a front-line orbital delocalization index of the hole-conducting segment represented by formula (1) and that of the hole-conducting segment represented by formula (2) is 3% or more.
3. The organic electroluminescent device according to claim 1 or 2, wherein a difference between a front-line orbital delocalization index of the hole-conducting segment represented by formula (1) and that of the hole-conducting segment represented by formula (2) is 20% or less.
4. The organic electroluminescent device according to claim 3, wherein a difference between the front-line orbital delocalization index of the hole-conducting segment represented by formula (1) and the hole-conducting segment represented by formula (2) is between 5 and 15%.
5. The organic electroluminescent device according to claim 4, wherein a difference between the front-line orbital delocalization index of the hole-conducting segment represented by formula (1) and the hole-conducting segment represented by formula (2) is between 8 and 12%.
6. The organic electroluminescent device according to claim 1 or 2, wherein the multi-hole transport channel material is a compound represented by formula (A1):
Therein, L, R 4 、R 5 、R 6 、R 7 Each represents a group as defined above; n is represented by the number 1, 2 or 3.
7. The organic electroluminescent device according to claim 1 or 2, wherein the multi-hole transport channel material is a compound represented by formula (A2):
therein, L, R 4 、R 5 、R 6 、R 7 Each represents a group as defined above;
n represents the number 1, 2 or 3;
a is C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl groups, or as fused rings with two adjacent carbon atoms in the carbazole group.
8. The organic electroluminescent device according to claim 1 or 2, wherein the multi-hole transport channel material is a compound represented by formula (A3):
therein, L, R 0 、R 4 、R 5 、R 6 、R 7 Each represents a group as defined above; n is represented by the number 1, 2 or 3.
9. The organic electroluminescent device according to claim 1 or 2, wherein the hole injection conductive film layer composition comprises a hole injection layer, a hole transport layer and an electron blocking layer, the hole injection layer and the hole transport layer comprising the same multi-hole transport channel material as in claim 1 or 2, and wherein the hole injection layer is a mixed film layer of the multi-hole transport channel material and a P-type doped material.
10. The organic electroluminescent device of claim 9, wherein a difference in HOMO levels between the electron blocking layer and the hole transporting layer is less than 0.3eV.
11. The organic electroluminescent device according to claim 9, wherein the electron blocking layer comprises a carbazole derivative represented by general formula (E):
wherein the method comprises the steps of
Ar 1 、Ar 2 Each independently represents substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
Ar 3 、Ar 4 each independently represented as a hydrogen atom, a substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
C. d is independently represented by a hydrogen atom, C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl, or represented as a fused ring with two adjacent carbon atoms in the carbazole group;
m represents the number 0, 1, 2 or 3;
wherein in the case of substitution, the substituents are independently selected from deuterium atoms, halogen atoms, C 1 -C 10 Alkoxy, adamantyl, cyano, C 1 -C 10 Alkyl, C 3 -C 20 Cycloalkyl, C 6 -C 30 Aryl, C containing one or more heteroatoms independently of one another selected from N, O and S 5 -C 30 Heteroaryl, or a combination thereof.
12. The organic electroluminescent device according to claim 11, wherein the electron blocking layer comprises a carbazole derivative represented by general formula (E1):
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 、Ar 2 each independently represents substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
Ar 3 、Ar 4 each independently represented as a hydrogen atom, a substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl, and Ar 3 、Ar 4 At least one of which is not represented as a hydrogen atom;
m represents the number 0, 1, 2 or 3.
13. The organic electroluminescent device according to claim 11, wherein the electron blocking layer comprises a carbazole derivative represented by general formula (E2):
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 、Ar 2 each independently represents substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl;
Ar 3 、Ar 4 each independently represented as a hydrogen atom, a substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 5 -C 30 Heteroaryl, and Ar 3 、Ar 4 At least one of which is not represented as a hydrogen atom;
C. d is independently represented by a hydrogen atom, C 6 -C 30 Aryl or C 5 -C 30 Heteroaryl, or represented as a fused ring with two adjacent carbon atoms in the carbazole group, and at least one of said C, D is not represented as a hydrogen atom;
m represents the number 0, 1, 2 or 3.
14. The organic electroluminescent device according to claim 1 or 2, wherein the light-emitting film layer composition comprises a host material and a guest material, wherein the host material comprises anthracene groups and the guest material is a fluorescent material.
15. The organic electroluminescent device according to claim 1 or 2, wherein the electron injection film layer comprises an electron transport layer and an electron injection layer, wherein the electron injection layer is an N-type metal material.
16. The organic electroluminescent device according to claim 1 or 2, wherein the multi-hole transport channel material of formula (a) is selected from any one of the following compounds:
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17. the organic electroluminescent device according to claim 1 or 2, wherein the multi-hole transport channel material of formula (B) is selected from any one of the following compounds:
18. a full-color display device comprising three pixels of red, green and blue, characterized in that the full-color display device comprises the organic electroluminescent device of any one of claims 1 to 17.
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