CN110391342B - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN110391342B CN110391342B CN201810344074.5A CN201810344074A CN110391342B CN 110391342 B CN110391342 B CN 110391342B CN 201810344074 A CN201810344074 A CN 201810344074A CN 110391342 B CN110391342 B CN 110391342B
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- hole transport
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- organic electroluminescent
- electroluminescent device
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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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—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
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—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
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Abstract
The invention relates to the technical field of display and discloses an organic electroluminescence deviceThe organic electroluminescent device comprises a cathode layer, an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, a hole injection layer and an anode layer, wherein the hole transport layer is made of heterocyclic hole transport materials, and the general formula of the heterocyclic hole transport materials is as follows:
the included angle of the dihedral angle between the two aromatic rings is 0 to 90 degrees; wherein the symbols used have the following meanings: r1、R2Identically or differently selected from O, S, N; r3、R4Is a hindering group for fine tuning of the dihedral angle; r5、R6The same or different groups are selected from aromatic rings, aromatic heterocycles, alkyl chains. In the above organic electroluminescent device, by adding a compound represented by formula (I) in R3、R4The group with larger connecting atomic nucleus increases the included angle of dihedral angles between the aromatic rings, improves the glass state transition temperature, further prolongs the service life of the organic electroluminescent device, and the heterocyclic cavity transport material has smaller molecular synthesis difficulty and lower cost.
Description
Technical Field
The invention relates to the technical field of display, in particular to an organic electroluminescent device.
Background
The structure of an OLED device is generally: the device comprises a cathode, an electron injection layer, an electron transport layer, a luminescent layer, a hole transport layer, a hole injection layer and an anode, wherein the key for improving the performance of the hole transport layer is to improve the glass transition temperature of the material, so that the service life of the device is prolonged.
At present, in the prior art, the glass transition temperature is improved mainly by three ways of increasing the molecular weight of a hole transport layer material or expanding the effective molecular weight of a molecule by utilizing a large non-planar molecule, such as triphenylamine, or utilizing an intermolecular hydrogen bond, but the above ways all need to achieve molecular design by more complex synthesis, so that the molecular synthesis difficulty is higher, and the cost is higher.
Disclosure of Invention
To overcome the disadvantages of the prior art, embodiments of the present invention provide an organic electroluminescent device by applying a voltage across R3、R4The group with larger connecting atomic nucleus increases the included angle of dihedral angle between the aromatic rings, increases the glass transition temperature, and further prolongs the length of the aromatic ringLifetime of the organic electroluminescent device.
In order to achieve the above object, the present invention provides an organic electroluminescent device, comprising a cathode layer, an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, a hole injection layer, and an anode layer, wherein the hole transport layer is made of a heterocyclic hole transport material, and the heterocyclic hole transport material has a general formula:
the included angle of the dihedral angle between the two aromatic rings is 0 to 90 degrees;
wherein the symbols used have the following meanings:
R1、R2identically or differently selected from O, S, N;
R3、R4is a hindering group for fine tuning of the dihedral angle;
R5、R6the same or different groups are selected from aromatic rings, aromatic heterocycles, alkyl chains.
In the above organic electroluminescent device, R3And R6There is a repulsive force, R, between the aromatic rings4And R5Repulsion exists between the aromatic rings, the two repulsion enable the positions of the two aromatic rings to deviate, so that the included angle of the dihedral angle between the aromatic rings can be adjusted, and when R is equal to R3When the atomic nucleus of the atom is small, R3And R6The repulsion between the aromatic rings is small when R is3When the nucleus of the atom is large, R3And R6The repulsion between the aromatic rings is large, and when R is equal to R4When the atomic nucleus of the atom is small, R4And R5The repulsion between the aromatic rings is small when R is4When the nucleus of the atom is large, R4And R5The repulsion between the aromatic rings is larger, when the repulsion between the aromatic rings is larger, the included angle of the dihedral angle is larger, and when the repulsion between the aromatic rings is smaller, the included angle of the dihedral angle is smaller; when the repulsion between the aromatic rings is larger, the glass transition temperature of the heterocyclic hole transport material is higher;
thus, by adding at R3、R4By linking groups of different nuclear sizes to the aromatic heterocyclic ring to regulate R3、R4The size of the included angle between the two aromatic rings is adjusted by the repulsive force between the aromatic rings, so that the glass transition temperature of the heterocyclic cavity transport material is improved by increasing the included angle between the two aromatic rings, the service life of the organic electroluminescent device is prolonged, the glass transition temperature is improved by increasing the included angle between the two aromatic rings, the molecular synthesis difficulty of the heterocyclic cavity transport material is low, and the cost is low.
Preferably, the included dihedral angle between the two aromatic rings shown in the formula of the heterocyclic hole transport material is in a range of 45 to 90 degrees.
Preferably, in the heterocyclic hole transport material: r3、R4Each of the aromatic rings, the aromatic heterocyclic rings and the alkyl chains.
Preferably, in the heterocyclic hole transport material: r3、R4Are all methyl.
Preferably, in the two phenyl rings shown in the heterocyclic hole transport material: one is connected with R7And the other is connected with R8And the structure of the heterocyclic hole transport material is as follows:
preferably, R3、R4、R7、R8At least one group is methyl.
Preferably, R3、R4、R7、R8Are all methyl.
Preferably, in the heterocyclic hole transport material: r3、R4、R7、R8At least one group contains boron element.
Preferably, R3、R4、R7、R8At least one group is a boronic acid group.
Preferably, R3、R4、R7、R8At least one group of (a) is boron fluoride.
Preferably, when R is1、R2Is N, R3、R4Is methyl, R5、R6When the two aromatic rings are included respectively, the hole transport material is:
drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings of the embodiments will be briefly described below, and it is apparent that the drawings in the following description only relate to some embodiments of the present invention and are not limiting to the present invention.
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention.
Icon: 1-a cathode layer; 2-an electron injection layer; 3-an electron transport layer; 4-a light-emitting layer; 5-a hole transport layer; 6-hole injection layer; 7-anode layer.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Referring to fig. 1, an organic electroluminescent device according to an embodiment of the present invention includes a cathode layer 1, an electron injection layer 2, an electron transport layer 3, a light emitting layer 4, a hole transport layer 5, a hole injection layer 6, and an anode layer 7, wherein the hole transport layer is made of a heterocyclic hole transport material, and the heterocyclic hole transport material has a general formula:
the included angle of the dihedral angle between the two aromatic rings is 0 to 90 degrees;
wherein the symbols used have the following meanings:
R1、R2identically or differently selected from O, S, N;
R3、R4a hindering group for fine tuning of dihedral angles;
R5、R6the same or different groups are selected from aromatic rings, aromatic heterocycles, alkyl chains.
In the above organic electroluminescent device, R3And R6There is a repulsive force, R, between the aromatic rings4And R5Repulsion exists between the aromatic rings, the two repulsion enable the positions of the two aromatic rings to deviate, so that the included angle of the dihedral angle between the aromatic rings can be adjusted, and when R is equal to R3When the atomic nucleus of the atom is small, R3And R6The repulsion between the aromatic rings is small when R is3When the nucleus of the atom is large, R3And R6The repulsion between the aromatic rings is large, and when R is equal to R4When the atomic nucleus of the atom is small, R4And R5The repulsion between the aromatic rings is small when R is4When the nucleus of the atom is large, R4And R5The repulsion between the aromatic rings is larger, when the repulsion between the aromatic rings is larger, the included angle of the dihedral angle is larger, and when the repulsion between the aromatic rings is smaller, the included angle of the dihedral angle is smaller; the higher the glass transition temperature of the heterocyclic hole transport material, the greater the aromatic ring repulsion;
thus, by adding at R3、R4By linking groups of different nuclear sizes to the aromatic heterocyclic ring to regulate R3、R4The size of the repulsion force between the aromatic rings is respectively adjusted to realize the adjustment of the dihedral angle included angle between the two aromatic rings, thereby realizing the increase of the dihedral angle included angle between the aromatic rings and the improvement of the glass transition temperature of the heterocyclic cavity transport materialAnd the glass transition temperature is increased by increasing the included angle of dihedral angles between the aromatic rings, so that the heterocyclic cavity transport material has low molecular synthesis difficulty and low cost.
Specifically, the included dihedral angle between two aromatic rings shown in the general formula of the heterocyclic hole transporting material is in the range of 45 to 90 degrees.
In the heterocyclic cavity transport material, when the included angle of the dihedral angle between two aromatic rings is between 45 degrees and 90 degrees, the synthesis cost of the material is low, and the glass transition temperature can be effectively increased.
Specifically, in the heterocyclic hole transport material: r3、R4Each of the aromatic rings, the aromatic heterocyclic rings and the alkyl chains.
In the above heterocyclic hole transport material, when R is3、R4The larger the nucleus, the larger the repulsion between the two benzene rings, and the larger the dihedral angle, resulting in a higher glass transition temperature.
Specifically, in the heterocyclic hole transport material: r3、R4Are all methyl.
Specifically, in the two benzene rings shown in the heterocyclic hole transport material: the structure of the heterocyclic hole transport material when one is connected and the other is connected is as follows:
in the heterocyclic hole transport material, R is provided in each aromatic heterocycle7And R8Increase by R3And R7Between radicals of (2), R4And R8The repulsion force existing between the groups increases the position offset between the two aromatic rings, thereby realizing the adjustment of the included angle of the dihedral angle between the aromatic rings by setting R7And R8Increase R3And R4The angle of the dihedral angle between the aromatic rings is increased with respect to the repulsive force between the benzene rings, so that the dihedral angle between the aromatic rings can be easily adjusted to a predetermined angle.
Specifically, R3、R4、R7、R8At least one group is methyl.
Specifically, R3、R4、R7、R8Are all methyl.
In the above structure, R3And R7Meta, R4And R8The repulsion exists in the middle methyl group, so that the two benzene rings are deviated under the action of the repulsion to form a dihedral angle with the degree being more than 0 degree.
Specifically, in the heterocyclic hole transport material: r3、R4、R7、R8At least one group contains boron element.
Specifically, R3、R4、R7、R8At least one group is a boronic acid group.
Specifically, R3、R4、R7、R8At least one group of (a) is boron fluoride.
In the heterocyclic hole material, a group containing a boron element is bonded at a position, and R is3、R7Repulsive force between and R4、R8The repulsion between the fragrance rings can adjust the dihedral angle of the fragrance rings.
Specifically, when R is1、R2Is N, R3、R4Is methyl, R5、R6When the two aromatic rings are respectively included in the material, the hole transport material is as follows:
it will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, if such modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include such modifications and variations.
Claims (7)
1. An organic electroluminescent device, comprising a cathode layer, an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, a hole injection layer, and an anode layer, wherein the hole transport layer is made of a heterocyclic hole transport material having the general formula:
the included angle of the dihedral angle between the two aromatic rings is 0 to 90 degrees;
wherein the symbols used have the following meanings:
R1、R2identically or differently selected from O, S, N;
R3、R4is a hindering group for fine tuning of the dihedral angle; r3、R4Respectively comprises at least one of aromatic ring, aromatic heterocycle and alkyl chain, or, R3、R4Are both methyl;
R5、R6the same or different groups are selected from aromatic rings, aromatic heterocycles, alkyl chains.
2. The organic electroluminescent device of claim 1, wherein the included dihedral angle between the two aromatic rings represented by the general formula of the heterocyclic hole transport material is in the range of 45 to 90 degrees.
3. The organic electroluminescent device according to claim 1, wherein the heterocyclic hole transport material has two benzene rings shown in the following: one is connected with R7And the other is connected with R8And the structure of the heterocyclic hole transport material is as follows:
R3、R4、R7、R8at least one radical of (A) is methyl, or, R3、R4、R7、R8At least one group contains boron element.
4. The organic electroluminescent device of claim 3, wherein R is3、R4、R7、R8Are all methyl.
5. The organic electroluminescent device of claim 3, wherein R is3、R4、R7、R8At least one group is a boronic acid group.
6. The organic electroluminescent device of claim 3, wherein R is3、R4、R7、R8At least one group of (a) is boron fluoride.
7. The organic electroluminescent device of claim 1, wherein when R is1、R2Is N, R3、R4Is methyl, R5、R6When the two aromatic rings are included respectively, the hole transport material is:
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104037361A (en) * | 2014-06-25 | 2014-09-10 | 上海道亦化工科技有限公司 | Organic electroluminescence device |
| CN106318378A (en) * | 2015-07-03 | 2017-01-11 | 上海和辉光电有限公司 | Organic electroluminescent compound and application thereof |
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| WO2015037548A1 (en) * | 2013-09-12 | 2015-03-19 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device |
| JP2015118958A (en) * | 2013-12-16 | 2015-06-25 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | Material for organic electroluminescence element and organic electroluminescence element using the same |
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| CN104037361A (en) * | 2014-06-25 | 2014-09-10 | 上海道亦化工科技有限公司 | Organic electroluminescence device |
| CN106318378A (en) * | 2015-07-03 | 2017-01-11 | 上海和辉光电有限公司 | Organic electroluminescent compound and application thereof |
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