CN110492010B - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN110492010B CN110492010B CN201810463721.4A CN201810463721A CN110492010B CN 110492010 B CN110492010 B CN 110492010B CN 201810463721 A CN201810463721 A CN 201810463721A CN 110492010 B CN110492010 B CN 110492010B
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- Prior art keywords
- organic electroluminescent
- electroluminescent device
- aromatic
- compound
- diketoboron
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- 238000002347 injection Methods 0.000 claims abstract description 30
- 239000007924 injection Substances 0.000 claims abstract description 30
- 230000005525 hole transport Effects 0.000 claims abstract description 23
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052796 boron Inorganic materials 0.000 claims abstract description 20
- 239000011365 complex material Substances 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- -1 diketone boron compound Chemical class 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 description 9
- 230000009477 glass transition Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
-
- 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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of display equipment and discloses an organic electroluminescent device which 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 hole injection layer or the hole transport layer is made of a boron complex. The organic electroluminescent device uses the boron complex material in a hole transport layer or a hole injection layer of the organic electroluminescent device, so that the voltage of the device can be reduced, and the efficiency and the service life of the device can be improved.
Description
Technical Field
The invention relates to the technical field of display equipment, in particular to an organic electroluminescent device.
Background
An organic electroluminescent device (OLED) has excellent characteristics of self-luminescence, high contrast, thin thickness, fast response speed, capability of being manufactured into a flexible panel, simple structure and the like. The general structure of an OLED device is: a Cathode (Cathode), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), an emission layer (EML), a Hole Transport Layer (HTL), a Hole Injection Layer (HIL), and an Anode (Anode).
There are also problems that need to be improved in current OLED devices, such as: the efficiency of the OLED device is improved; the service life of the OLED device is prolonged; the operating voltage of the OLED device is reduced, and the like, and the solution of these problems mainly depends on the design development of novel OLED organic materials, and there are several main directions: the high carrier migration rate can reduce the driving voltage of the device and improve the efficiency of the device; the thermal stability is good at the long-time evaporation temperature, which is very important for the industrial production of the OLED; high glass transition temperature (Tg), which tends to form amorphous films under suitable conditions, is critical for device lifetime; the material is easy to prepare and purify, the cost can be reduced, and the economic benefit can be increased.
The materials of the current Hole Transport Layer (HTL) and Hole Injection Layer (HIL) are basically in the following categories: triarylamine derivatives, spirobifluorene derivatives, carbazole derivatives, and the like. However, in order to meet the increasing device performance requirements, it is necessary to develop a novel hole transport material having characteristics of high material thermal stability, high Tg temperature, high carrier mobility, and good solubility in organic solvents.
Disclosure of Invention
The invention provides an organic electroluminescent device, which uses a boron complex material in a hole transport layer or a hole injection layer of the organic electroluminescent device to reduce the voltage of the device and improve the efficiency and the service life of the device.
In order to achieve the purpose, the invention provides the following technical scheme:
an organic electroluminescent 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 hole injection layer or the hole transport layer is made of a boron complex material.
The organic electroluminescent 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 hole injection layer or the hole transport layer is made of a boron complex. The boron complex has better thermal stability, excellent electrochemical stability and certain electrophilicity, so that the boron complex material has excellent photophysical chemical properties, and the application of the boron complex material in a hole transport layer or a hole injection layer of an organic electroluminescent device can reduce the voltage of the device and improve the efficiency and the service life of the device.
Preferably, the boron complex is a diketone boron compound taking beta-diketone boron as a framework, and the general formula of the diketone boron compound is as follows:
wherein Ar is1、Ar2Is an aromatic group;
Ar3、Ar4either aromatic or aliphatic.
Preferably, Ar in the diketoboron compound1、Ar2、Ar3And Ar4Is an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms.
Preferably, Ar in the diketoboron compound1、Ar2、Ar3And Ar4Is aryloxy having 5 to 60 aromatic ring atomsOr a heteroaryloxy group.
Preferably, Ar in the diketoboron compound3And Ar4Joined to form an integral aromatic or aliphatic ring system.
Preferably, Ar in the diketoboron compound3And Ar4Is not connected.
Preferably, the diketoboron compound has the general formula:
alternatively, the first and second electrodes may be,
wherein Ar is1、Ar2Is an aromatic group.
Preferably, Ar in the diketoboron compound3、Ar4Are two independent aromatic radicals, Ar3And Ar4Have a twist angle of 0 to 90 degrees therebetween.
Preferably, by adjusting Ar3And Ar4Size adjustment of two aromatic rings Ar3And Ar4To adjust the flatness of the diketoboron compound molecules.
Preferably, by adjusting Ar3And Ar4Number of aromatic ring atoms of two aromatic rings, or, by adjusting Ar3And Ar4Quantity adjustment of methyl groups on two aromatic rings Ar3And Ar4Size of aromatic ring.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention.
Icon: 1-a cathode; 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.
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, the present invention provides an organic electroluminescent device, which includes a cathode 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, an anode 7, and a material for manufacturing the hole injection layer 6 or the hole transport layer 5 is a boron complex material.
The organic electroluminescent device provided by the above embodiment of the present invention includes a cathode 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 7, wherein the hole injection layer 6 or the hole transport layer 5 is made of a boron complex. The boron complex has better thermal stability, excellent electrochemical stability and certain electrophilicity, so that the boron complex material has excellent photophysical chemical properties, and the application of the boron complex material in a hole transport layer or a hole injection layer of an organic electroluminescent device can reduce the voltage of the device and improve the efficiency and the service life of the device.
In the above-described embodiment of the present invention, preferably, the boron complex may be a diketoboron compound having β -diketoboron as a skeleton, and the general formula of the diketoboron compound may be written as:
wherein Ar is1、Ar2Represents an aromatic group; ar (Ar)3、Ar4Represents aromatic or aliphatic. The boron complex material is used for a hole transport layer or a hole injection layer of an organic electroluminescent device, so that the voltage of the device is reduced, the efficiency of the device is improved, and the service life of the device is prolonged.
Specifically, Ar in the diketoboron compound1、Ar2、Ar3And Ar4Can represent aromatic or heteroaromatic ring systems having from 5 to 60 aromatic ring atoms, which makes the range of materials available in the hole transport layer or the hole injection layer of organic electroluminescent devices even more extensive.
Specifically, Ar in the diketoboron compound1、Ar2、Ar3And Ar4Is also an aryloxy or heteroaryloxy group having from 5 to 60 aromatic ring atoms. Thereby making the range of materials available in the hole transport layer or hole injection layer of the organic electroluminescent device much broader.
In the above-mentioned embodiment of the invention, Ar in the diketoboron compound3And Ar4May be linked to form an integral aromatic ring system or aliphatic. For example, one of them represents Ar3And Ar4One molecular formula in the linked state is:
in the above-mentioned embodiment of the invention, Ar in the diketoboron compound3And Ar4Not also connected, i.e. Ar3，Ar4Either as separate aliphatic or aromatic ring systems or joined together to form an integral aliphatic or aromatic ring system, making the choice of diketoboron compound materials more versatile.
When Ar is present in diketoboron compounds3And Ar4When not attached, one of the diketoboron compounds can be represented by the general formula:
alternatively, the first and second electrodes may be,
wherein Ar is1、Ar2Is an aromatic group. To say thatIt is to be understood that the above formula does not represent all Ar3And Ar4In case of no connection, Ar3And Ar4It may be the case otherwise when not connected.
In the above-mentioned embodiment of the invention, Ar in the diketoboron compound3、Ar4When two independent aromatic groups are present, Ar3And Ar4Have a twist angle of 0 to 90 degrees therebetween. Ar in diketoboron compounds3And Ar4The different torsion angles are different, and the flatness of the diketone boron compound molecules is different.
Specifically, Ar can be adjusted3And Ar4Size adjustment of two aromatic rings Ar3And Ar4The twist angle therebetween to adjust the flatness of the diketoboron compound molecule. Among the material parameters of the organic electroluminescent device, the uneven molecular structure is beneficial to increase the glass transition temperature of the molecules.
In particular, by adjusting Ar3And Ar4Number of aromatic ring atoms of two aromatic rings, or, by adjusting Ar3And Ar4Quantity adjustment of methyl groups on two aromatic rings Ar3And Ar4Size of aromatic ring. For example, Ar3Having a methyl group, and Ar4With two methyl groups, Ar3And Ar4The number of methyl groups on the two aromatic rings being different, leading to Ar3And Ar4The size of the aromatic ring is varied by adjusting Ar3And Ar4Size adjustment of aromatic Ring Ar3And Ar4The size of the torsion angle between the two parts, and further the glass transition temperature of the molecules is adjusted.
It will be apparent to those skilled in the art that various changes and modifications may be made in the embodiments of 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 (9)
1. An organic electroluminescent 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, and is characterized in that the hole injection layer or the hole transport layer is made of a boron complex material;
the boron complex is a diketone boron compound taking beta-diketone boron as a framework, and the general formula of the diketone boron compound is as follows:
wherein Ar is1、Ar2Is an aromatic group;
Ar3、Ar4either aromatic or aliphatic.
2. The organic electroluminescent device as claimed in claim 1, wherein Ar in the diketoboron compound is Ar1、Ar2、Ar3And Ar4Is an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms.
3. The organic electroluminescent device as claimed in claim 1, wherein Ar in the diketoboron compound is Ar1、Ar2、Ar3And Ar4Is an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms.
4. The organic electroluminescent device as claimed in claim 1, wherein Ar in the diketoboron compound is Ar3And Ar4Joined to form an integral aromatic or aliphatic ring system.
5. The organic electroluminescent device as claimed in claim 1, wherein Ar in the diketoboron compound is Ar3And Ar4Is not connected.
6. The organic electroluminescent device of claim 5, wherein the diketoboron compound has the formula:
alternatively, the first and second electrodes may be,
wherein Ar1 and Ar2 are aromatic groups.
7. The organic electroluminescent device as claimed in claim 5, wherein Ar in the diketoboron compound is Ar3、Ar4Are two independent aromatic radicals, Ar3And Ar4Have a twist angle of 0 to 90 degrees therebetween.
8. The organic electroluminescent device of claim 7, wherein the Ar is adjusted by adjusting Ar3And Ar4Size adjustment of two aromatic rings Ar3And Ar4To adjust the flatness of the diketoboron compound molecules.
9. The organic electroluminescent device of claim 8, wherein the Ar is adjusted by adjusting Ar3And Ar4Number of aromatic ring atoms of two aromatic rings, or, by adjusting Ar3And Ar4Quantity adjustment of methyl groups on two aromatic rings Ar3And Ar4Size of aromatic ring.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810463721.4A CN110492010B (en) | 2018-05-15 | 2018-05-15 | Organic electroluminescent device |
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| CN201810463721.4A CN110492010B (en) | 2018-05-15 | 2018-05-15 | Organic electroluminescent device |
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| CN110492010B true CN110492010B (en) | 2022-01-07 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006048679A2 (en) * | 2004-11-05 | 2006-05-11 | Oled-T Limited | Electroluminescent complexes |
| CN104311601A (en) * | 2013-03-02 | 2015-01-28 | 大连理工大学 | Pyrazine-based ring metal ligand-platinum complex as well as preparation method and application thereof |
| CN105009316A (en) * | 2013-02-28 | 2015-10-28 | 新日铁住金化学株式会社 | Boron compound for organic electroluminescent elements, and organic electroluminescent element |
| US20180298034A1 (en) * | 2015-03-10 | 2018-10-18 | Korea Research Institute Of Chemical Technology | Method for Preparing Four-Coordinated Organic Boron Compound |
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2018
- 2018-05-15 CN CN201810463721.4A patent/CN110492010B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006048679A2 (en) * | 2004-11-05 | 2006-05-11 | Oled-T Limited | Electroluminescent complexes |
| CN105009316A (en) * | 2013-02-28 | 2015-10-28 | 新日铁住金化学株式会社 | Boron compound for organic electroluminescent elements, and organic electroluminescent element |
| CN104311601A (en) * | 2013-03-02 | 2015-01-28 | 大连理工大学 | Pyrazine-based ring metal ligand-platinum complex as well as preparation method and application thereof |
| US20180298034A1 (en) * | 2015-03-10 | 2018-10-18 | Korea Research Institute Of Chemical Technology | Method for Preparing Four-Coordinated Organic Boron Compound |
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