CN114256430A - Electroluminescent device - Google Patents

Electroluminescent device Download PDF

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CN114256430A
CN114256430A CN202110464966.0A CN202110464966A CN114256430A CN 114256430 A CN114256430 A CN 114256430A CN 202110464966 A CN202110464966 A CN 202110464966A CN 114256430 A CN114256430 A CN 114256430A
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CN114256430B (en
Inventor
王乐
王强
王俊飞
张晗
张奇
代志洪
张翠芳
路楠楠
邝志远
夏传军
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Beijing Summer Sprout 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
    • 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
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
    • 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

Abstract

An electroluminescent device is disclosed. The electroluminescent device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including at least a first compound having an H-L-E structure and an organic compound having M (L)a)m(Lb)n(Lc)qA second compound of formula (la). The novel material combination consisting of the first compound and the second compound can enable an electroluminescent device to obtain lower voltage, higher efficiency and ultra-long service life, and can provide better device performance. Also disclosed are an electronic device and a compound combination.

Description

Electroluminescent device
Technical Field
The present invention relates to electronic devices, such as electroluminescent devices. More particularly, it relates to a composition comprising a first compound having H-L-E structure and a second compound having M (L) in an organic layera)m(Lb)n(Lc)qAn electroluminescent device comprising a novel combination of materials of a second compound of formula (I).
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.
In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.
Various OLED manufacturing methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing and nozzle printing. Small molecule OLEDs can also be made by solution processes if the material can be dissolved or dispersed in a solvent.
The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have the problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full-color OLED displays typically employ a hybrid strategy, using either blue fluorescence and phosphorescent yellow, or red and green. At present, the rapid decrease in efficiency of phosphorescent OLEDs at high luminance is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
For the development of phosphorescent OLEDs, it is an important and extensive research direction to select suitable host materials for use with phosphorescent light-emitting materials.
KR1020150077220A discloses a composition containing
Figure BDA0003043795300000021
Compounds of the general structure, specific examples being
Figure BDA0003043795300000022
Although it is claimed that these two compounds are synthesized, the key intermediates provided are
Figure BDA0003043795300000023
The characterization data of (a) do not correspond to the structure of this compound, and therefore it remains doubtful whether both compounds are obtained. In addition, in this application it is only mentioned that the following luminescent materials can be used in combination
Figure BDA0003043795300000024
However, it does not address the issue of matching host materials with luminescent materials, nor does it disclose and teach that the disclosed host materials can be used with luminescent materials of other configurations.
US20180337340a1 discloses an organic electroluminescent compound and an organic electroluminescent device comprising the same, comprising an organic layer comprising one or more hosts, the first host of which is an organic optical compound having the structure:
Figure BDA0003043795300000025
the compounds disclosed therein must have a structural element of quinazoline or quinoxaline. In addition, this application uses in device comparative examples
Figure BDA0003043795300000031
The inventors of the present application have not found that excellent properties can be obtained by reasonably selecting a novel material combination in which a host compound having a triazine structure and the like is collocated with a suitable phosphorescent light-emitting compound. The teaching in this application in the comparative examples is essentially contrary to the present application.
However, the device performance of the combination of the host material and the phosphorescent light-emitting material reported at present still has room for improvement, and in order to meet the increasing demand in the industry, selecting a suitable combination of the host material and the phosphorescent light-emitting material is a relatively efficient research and development means, and further research and development of a novel material combination is still needed.
Disclosure of Invention
The present invention aims to solve at least part of the above problems by providing an electroluminescent device with a novel combination of materials. The electroluminescent device comprises a first compound having H-L-E structure and a second compound having M (L)a)m(Lb)n(Lc)qThe novel material combination consisting of the second compound of the general formula can be used in a light-emitting layer of an electroluminescent device. The novel material combination can enable the electroluminescent device to obtain lower voltage, higher efficiency and ultra-long service life, and can provide better device performance.
According to one embodiment of the present invention, an electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including at least a first compound and a second compound;
the first compound has the structure of H-L-E;
h has a structure represented by formula 1:
Figure BDA0003043795300000032
in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rfthe same or different at each occurrence denotes mono-, poly-or no-substitution;
e has a structure represented by formula 2:
Figure BDA0003043795300000033
in formula 2, Z1To Z5At least one of which is N and the others are each independently selected from CRz；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R，Rfand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted alkane having 3 to 20 carbon atoms.A silicon group, a substituted or unsubstituted arylsilane group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring;
the second compound is a metal complex having M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein M is selected from metals having a relative atomic mass greater than 40;
La、Lb、Lca first ligand, a second ligand and a third ligand which are respectively coordinated with the M; l isa、Lb、LcOptionally linked to form a multidentate ligand;
La、Lb、Lcmay be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of LaMay be the same or different; when n is 2, two LbMay be the same or different;
Lahas a structure as shown in formula 3:
Figure BDA0003043795300000041
wherein the content of the first and second substances,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring D and ring E via YaAnd YbFusing;
Yaand YbSelected from C or N, identically or differently at each occurrence;
Rd，Rethe same or different at each occurrence denotes mono-, poly-or unsubstituted;
X1-X4selected from CR, identically or differently at each occurrencexOr N;
Rd，Re，Rxeach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rd，Re，RxCan be optionally connected to form a ring;
Lband LcEach independently selected from any one of the following structures:
Figure BDA0003043795300000051
Ra，Rband RcThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xbselected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach independently selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
at LbAnd LcIn the structure (1), adjacent substituents Ra，Rb，Rc，RN1，RN2，RC1And RC2Can optionally be linked to form a ring;
and does not include the following: the first compound is
Figure BDA0003043795300000052
While the second compound is
Figure BDA0003043795300000053
According to another embodiment of the present invention, there is also disclosed a display device comprising the electroluminescent device as described above.
According to another embodiment of the present invention, there is also disclosed a combination of compounds comprising a first compound and a second compound;
the first compound has the structure of H-L-E;
h has a structure represented by formula 1:
Figure BDA0003043795300000061
in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rfthe same or different at each occurrence denotes mono-, poly-or no-substitution;
e has a structure represented by formula 2:
Figure BDA0003043795300000062
in formula 2, Z1To Z5At least one of which is N and the others are each independently selected from CRz；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R，Rfand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atomsAn alkylsilyl group of 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6-20 carbon atoms, a substituted or unsubstituted amino group of 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring;
the second compound is a metal complex having M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein M is selected from metals having a relative atomic mass greater than 40;
La、Lb、Lca first ligand, a second ligand and a third ligand which are respectively coordinated with the M; l isa、Lb、LcOptionally linked to form a multidentate ligand;
La、Lb、Lcmay be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of LaMay be the same or different; when n is 2, two LbMay be the same or different;
Lahas a structure as shown in formula 3:
Figure BDA0003043795300000071
wherein the content of the first and second substances,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring D and ring E via YaAnd YbFusing;
Yaand YbSelected from C or N, identically or differently at each occurrence;
Rd，Rethe same or different at each occurrence denotes mono-, poly-or unsubstituted;
X1-X4selected from CR, identically or differently at each occurrencexOr N;
Rd，Re，Rxeach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rd，Re，RxCan be optionally connected to form a ring;
Lband LcEach independently selected from any one of the following structures:
Figure BDA0003043795300000072
Ra，Rband RcThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xbselected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach independently selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
at LbAnd LcIn the structure (1), adjacent substituents Ra，Rb，Rc，RN1，RN2，RC1And RC2Can optionally be linked to form a ring;
and does not include the following: the first compound is
Figure BDA0003043795300000081
While the second compound is
Figure BDA0003043795300000082
The invention discloses a novel electroluminescent device, which uses a first compound with H-L-E structure and a second compound with M (L)a)m(Lb)n(Lc)qNovel material combinations consisting of a second compound of the general formulaThe novel material combinations can be used in the light-emitting layer of electroluminescent devices. The novel material combination can enable the novel electroluminescent device to obtain lower voltage, higher efficiency and ultra-long service life, and can provide better device performance.
Drawings
Fig. 1 is a schematic diagram of an organic light emitting device that may contain electroluminescent devices as disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that may contain electroluminescent devices as disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:14TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose the practice of cathodesFor example, it comprises a composite cathode having a thin layer of a metal such as Mg: Ag with an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ ES-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).
Definitions for substituent terms
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-as used herein, includes both straight and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.
Cycloalkyl-as used herein, comprises a cyclic alkyl group. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl are preferable. In addition, the cycloalkyl group may be optionally substituted.
Heteroalkyl-as used herein, heteroalkyl comprises a alkyl chain wherein one or more carbons are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxyethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. In addition, heteroalkyl groups may be optionally substituted.
Alkenyl-as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 3-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group, a 3-phenyl-1-butenyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cycloheptenyl group, a cycloheptatrienyl group, a cyclooctenyl group, a cyclooctatetraenyl group and a norbornenyl group. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight chain alkynyl groups are contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,
Figure BDA0003043795300000101
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.
Heterocyclyl or heterocyclic-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuryl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. In addition, the heterocyclic group may be optionally substituted.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indoline, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, cinnolino, benzoselenophenopyridine, selenobenzene, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.
Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy groups may be optionally substituted.
Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include a phenoxy group and a biphenyloxy group. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable. In addition, the aralkyl group may be optionally substituted.
Alkylsilyl-as used herein, alkyl substituted silyl is contemplated. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethylisopropylsilyl group, tri-tert-butylsilyl group, triisobutylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. Additionally, the alkylsilyl group may be optionally substituted.
Arylsilyl-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl group, phenylbiphenylsilyl group, diphenylbiphenylsilyl group, phenyldiethylsilyl group, diphenylethylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, phenyldiisopropylsilyl group, diphenylisopropylsilyl group, diphenylbutylsilyl group, diphenylisobutylsilyl group, diphenyltert-butylsilyl group, tri-tert-butylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. In addition, the arylsilyl group may be optionally substituted.
The term "aza" in azabenzofuran, azabenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which may be substituted with one or more substituents selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
Figure BDA0003043795300000131
the expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
Figure BDA0003043795300000132
further, the expression that adjacent substituents can be optionally connected to form a ring is also intended to be taken to mean that, in the case where one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at a position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
Figure BDA0003043795300000133
according to one embodiment of the present invention, there is disclosed an electroluminescent device comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound;
the first compound has the structure of H-L-E;
h has a structure represented by formula 1:
Figure BDA0003043795300000134
in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rfthe same or different at each occurrence denotes mono-, poly-or no-substitution;
e has a structure represented by formula 2:
Figure BDA0003043795300000135
in formula 2, Z1To Z5At least one of which is N and the others are each independently selected from CRz；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R，Rfand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring;
the second compound is a metal complex having M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
m is selected from metals having a relative atomic mass greater than 40;
La、Lb、Lca first ligand, a second ligand and a third ligand which are respectively coordinated with the M; l isa、Lb、LcOptionally linked to form a multidentate ligand; for example, La、LbAnd LcAny two of which can be linked to form a tetradentate ligand; also for example, La、LbAnd LcCan be connected with each other to form a hexadentate ligand; or also for example La、Lb、LcAre not linked so as not to form a multidentate ligand;
La、Lb、Lcmay be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of LaMay be the same or different; when n is 2, two LbMay be the same or different;
Lahas a structure as shown in formula 3:
Figure BDA0003043795300000141
wherein the content of the first and second substances,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring D and ring E via YaAnd YbFusing;
Yaand YbSelected from C or N, identically or differently at each occurrence;
Rd，Rethe same or different at each occurrence denotes mono-, poly-or unsubstituted;
X1-X4selected from CR, identically or differently at each occurrencexOr N;
Rd，Re，Rxeach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstitutedAn alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
adjacent substituents Rd，Re，RxCan be optionally connected to form a ring;
Lband LcEach independently selected from any one of the following structures:
Figure BDA0003043795300000151
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Xbselected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach independently selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl having 3-A cycloalkyl group of 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
at LbAnd LcIn the structure (1), adjacent substituents Ra，Rb，Rc，RN1，RN2，RC1And RC2Can optionally be linked to form a ring;
and does not include the following: the first compound is
Figure BDA0003043795300000152
While the second compound is
Figure BDA0003043795300000153
In this context, the adjacent substituents R, RfCan optionally be linked to form a ring, intended to indicate when a substituent R, R is presentfWhere adjacent substituent groups, e.g. between adjacent substituents R, adjacent substituents RfAnd the substituents R and RfAny one or more of these adjacent substituent groups can be linked to form a ring. Obviously, when the substituent R, the substituent R is presentfIn the case of the above, none of these substituent groups may be linked to form a ring.
In this context, adjacent substituents Rd，Re，RxCan optionally be linked to form a ring, intended to indicate when a substituent R is presentdA substituent ReA substituent RxIn which adjacent substituent groups, e.g. adjacent substituent groups RdAdjacent and adjacent substituents ReAdjacent and adjacent substituents RxAdjacent and adjacent substituents RdAnd ReAdjacent and adjacent substituents RdAnd RxThe substituents R between, and adjacent toeAnd RxAny one or more of these adjacent substituent groups can be linked to form a ring. Obviously, when the substituent R is presentdA substituent ReA substituent RxIn the case of the above, none of these substituent groups may be linked to form a ring.
In this context, at LbAnd LcIn the structure (1), adjacent substituents Ra，Rb，Rc，RN1，RN2，RC1And RC2Can optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents RaIn between, two substituents RbIn between, two substituents RcOf a substituent RaAnd RbOf a substituent RaAnd RcOf a substituent RbAnd RcOf a substituent RaAnd RN1Of a substituent RbAnd RN1Of a substituent RaAnd RC1Of a substituent RaAnd RC2Of a substituent RbAnd RC1Of a substituent RbAnd RC2Of a substituent RaAnd RN2Of a substituent RbAnd RN2And R isC1And RC2And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the present invention, wherein, in said formula 1, ring a, ring B and ring C, identically or differently at each occurrence, are selected from aromatic rings having 6 to 18 carbon atoms, or heteroaromatic rings having 3 to 18 carbon atoms.
According to one embodiment of the present invention, wherein, in said formula 1, ring a, ring B and ring C, identically or differently at each occurrence, are selected from aromatic rings having 6 to 12 carbon atoms, or heteroaromatic rings having 3 to 12 carbon atoms.
According to one embodiment of the present invention, wherein, in said formula 1, ring a, ring B and ring C, which may be the same or different at each occurrence, are selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring.
According to an embodiment of the present invention, wherein, in the first compound, the H has a structure represented by formula 1-a:
Figure BDA0003043795300000161
wherein A is1To A3Selected, identically or differently, on each occurrence from N or CR, F1To F10Selected from CR, identically or differently at each occurrencefOr N;
R，Rfeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring.
According to an embodiment of the invention, wherein in the first compound, RfEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring.
According to one embodiment of the invention, wherein in the first compound, R and RfAt least one of which is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
preferably, R and RfAt least one of which is selected from deuterium, phenyl, biphenyl, or pyridyl.
According to one embodiment of the invention, wherein, in the first compound, A1To A3Adjacent substituents R, F between1To F3Adjacent substituent R betweenf，F4To F6Adjacent substituent R betweenfAnd F7To F10Adjacent substituent R betweenfAt least one of these adjacent substituent groups is linked to form a ring.
According to an embodiment of the invention, wherein in the first compound, the H is selected from the group consisting of the following structures:
Figure BDA0003043795300000171
Figure BDA0003043795300000181
Figure BDA0003043795300000191
according to one embodiment of the invention, wherein the hydrogen in the structure of H-1 to H-57 can be partially or completely substituted with deuterium.
According to an embodiment of the present invention, wherein, in the first compound, the E has a structure represented by any one of formulae 2-a to 2-h:
Figure BDA0003043795300000192
wherein Z is1To Z5Selected from CR, identically or differently at each occurrencez；
Wherein R iszEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl groupSulfonyl, phosphino, and combinations thereof.
According to a preferred embodiment of the invention, wherein RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
According to a preferred embodiment of the invention, wherein RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, pyridyl, and combinations thereof.
According to one embodiment of the invention, wherein in the first compound, E is selected from substituted or unsubstituted triazinyl.
According to an embodiment of the invention, wherein in the first compound, wherein E is selected from the group consisting of the following structures:
Figure BDA0003043795300000201
Figure BDA0003043795300000211
Figure BDA0003043795300000221
wherein in the above structure
Figure BDA0003043795300000222
Indicating the location where the structure is attached to the L structure.
According to one embodiment of the invention, wherein the hydrogen in the structure of E-1 to E-69 can be partially or completely substituted with deuterium.
According to one embodiment of the present invention, wherein in the first compound, L is selected from a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to an embodiment of the invention, wherein in the first compound, the L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, phenanthrylene, and fluorenylene.
According to an embodiment of the invention, wherein in the first compound, the L is selected from the group consisting of the following structures: single bond
Figure BDA0003043795300000223
Figure BDA0003043795300000224
Wherein "+" in the above structure denotes a position where the structure is connected to the H structure,
Figure BDA0003043795300000231
indicating the location of the attachment of the structure to the E structure.
According to one embodiment of the present invention, wherein hydrogen in the structure of L-1 to L-28 can be partially or completely substituted with deuterium.
According to one embodiment of the present invention, wherein the first compound is selected from the group consisting of compound 1 to compound 520, and the specific structures of the compound 1 to compound 520 are shown in claim 9.
According to an embodiment of the invention, wherein in the second compound, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.
According to an embodiment of the invention, wherein M in the second compound is selected from Ir, Pt or Os.
According to an embodiment of the invention, wherein M is Ir in the second compound.
According to an embodiment of the present invention, wherein, in the second compound, the LaHaving the formula 3-1 to a structure represented by any one of formulae 3-5:
Figure BDA0003043795300000232
wherein the content of the first and second substances,
ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
Rethe same or different at each occurrence denotes mono-, poly-or no-substitution;
X11-X14selected from CR, identically or differently at each occurrencex1Or N; x21-X24Selected from CR, identically or differently at each occurrencex2Or N; x31-X34Selected from CR, identically or differently at each occurrencex3Or N; x41-X44Selected from CR, identically or differently at each occurrencex4Or N; x51-X54Selected from CR, identically or differently at each occurrencex5Or N;
y is selected, identically or differently on each occurrence, from O, S, Se, NRd1，CRd1Rd1Or SiRd1Rd1(ii) a When two R are simultaneously presentd1When two R are presentd1May be the same or different; for example, when Y is selected from CRd1Rd1When two R are presentd1May be the same or different; as another example, when Y is selected from SiRd1Rd1When two R are presentd1May be the same or different;
preferably, Y is selected, identically or differently on each occurrence, from O or S;
Y3and Y4Selected from CR, identically or differently at each occurrencedOr N;
Rx1、Rx2、Rx3、Rx4、Rx5、Rd1、Rdand ReEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstitutedSubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Rx1、Rx2、Rx4、Rx5、Rd1、RdAnd ReCan optionally be linked to form a ring;
when R isx3Selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or substituted or unsubstituted amino groups having 0 to 20 carbon atoms, adjacent substituents Rx3Can optionally be linked to form a ring.
In this context, adjacent substituents Rx1、Rx2、Rx4、Rx5、Rd1、RdAnd ReCan optionally be linked to form a ring, intended to indicate when a substituent R is presentx1A substituent Rx2A substituent Rx4A substituent Rx5A substituent ReA substituent RdOr a substituent Rd1In which adjacent substituent groups are present, e.g.Adjacent substituents Rx1Adjacent and adjacent substituents Rx2Adjacent and adjacent substituents Rx4Adjacent and adjacent substituents Rx5Adjacent and adjacent substituents Rd1Meta, substituent Rx1And RdMeta, substituent Rx1And ReMeta, substituent Rx2And RdMeta, substituent Rx3And RdMeta, substituent Rx4And ReMeta, substituent Rx5And Rd1Meta, substituent Rd1And ReAnd a substituent RdAnd ReAny one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
In this context, when Rx3When selected from the substituent group, adjacent substituents Rx3Can optionally be linked to form a ring, intended to indicate when a substituent R is presentx3And the substituent Rx3When selected from the group consisting of alkyl, cycloalkyl, aralkyl, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl and amino, adjacent substituents Rx3Can be connected to form a ring; when the substituent R isx3When a substituent selected from the above-mentioned substituent groups is other than the above-mentioned substituent group, the adjacent substituent Rx3Cannot be connected to form a ring. Obviously, when the substituent R isx3When selected from the above substituent groups, adjacent substituents Rx3Or may be both unconnected to form a ring.
According to an embodiment of the invention, wherein, in the second compound, wherein L isaHas a structure represented by any one of formulas 3-6 to 3-13:
Figure BDA0003043795300000241
wherein the content of the first and second substances,
X11-X14selected from CR, identically or differently at each occurrencex1Or N; x21-X24Identical or different at each occurrenceIs selected from CR togetherx2Or N; x31-X34Selected from CR, identically or differently at each occurrencex3Or N; x41-X44Selected from CR, identically or differently at each occurrencex4Or N; x51-X54Selected from CR, identically or differently at each occurrencex5Or N;
Y3and Y4Selected from CR, identically or differently at each occurrencedOr N;
Y5、Y6、Y7and Y8Selected from CR, identically or differently at each occurrenceeOr N;
y is selected, identically or differently on each occurrence, from O, S, Se, NRd1，CRd1Rd1Or SiRd1Rd1(ii) a When two R are simultaneously presentd1When two R are presentd1May be the same or different; for example, when Y is selected from CRd1Rd1When two R are presentd1May be the same or different; as another example, when Y is selected from SiRd1Rd1When two R are presentd1May be the same or different;
Rx1、Rx2、Rx3、Rx4、Rx5、Rd1、Rdand ReEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl groupCarbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents Rx1、Rx2、Rx4、Rx5、Rd1、RdAnd ReCan optionally be linked to form a ring;
when R isx3Selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or substituted or unsubstituted amino groups having 0 to 20 carbon atoms, adjacent substituents Rx3Can optionally be linked to form a ring.
According to an embodiment of the present invention, wherein said LaHas a structure as shown in any one of formulas 3-6 to 3-13, wherein said Y is selected from O or S, the same or different at each occurrence.
According to an embodiment of the present invention, wherein said LaHas a structure shown in formula 3-6, formula 3-7, formula 3-9, formula 3-10, formula 3-11, formula 3-12 or formula 3-13.
According to an embodiment of the present invention, wherein said LaHas a structure as shown in formula 3-6 or formula 3-9.
According to an embodiment of the present invention, wherein, in formulae 3-6 to 3-11, Y3-Y4Is N.
According to an embodiment of the present invention, wherein Y is represented by formula 3-6, formula 3-7, formula 3-9, formula 3-10, and formula 3-114Is N; in the formulae 3 to 8Y3Is N.
According to an embodiment of the present invention, wherein, in formulae 3-6 to 3-13, Y3And Y4Selected from CR, identically or differently at each occurrenced；Y5、Y6、Y7And Y8Selected from CR, identically or differently at each occurrencee。
According to an embodiment of the present invention, wherein, in formulae 3-6 to 3-13, Y3And/or Y4Selected from the group consisting of CRdAnd said R isdEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having from 0 to 20 carbon atoms.
According to an embodiment of the present invention, wherein, in formulae 3-6 to 3-13, Y3And/or Y4Selected from the group consisting of CRdAnd said R isdEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulae 3-6 to 3-13, Y5-Y8At least one or two of which are selected from CReAnd said R iseEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having from 0 to 20 carbon atoms.
According to an embodiment of the present invention, wherein, in formulae 3-6 to 3-13, Y5-Y8At least one or two of which are selected from CReAnd said R iseEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulae 3-6 and formulae 3-9, Y6Selected from the group consisting of CRe(ii) a In the formulae 3 to 8, Y4Selected from the group consisting of CRdAnd/or Y6-Y8At least one of which is selected from CRe(ii) a In formulae 3-10 and 3-11, Y5And Y6At least one of which is CRe(ii) a And said R isd，ReIdentical or different at each occurrenceIs selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having from 0 to 20 carbon atoms.
According to an embodiment of the present invention, wherein, in formulae 3-6 and formulae 3-9, Y6Selected from the group consisting of CRe(ii) a In the formulae 3 to 8, Y4Selected from the group consisting of CRdAnd/or Y6-Y8At least one of which is selected from CRe(ii) a In formulae 3-10 and 3-11, Y5And Y6At least one of which is CRe(ii) a And said R isd，ReEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulae 3-10 and formulae 3-11, Y5And Y6At least one of which is selected from CReAnd said R iseEach occurrence, identically or differently, is selected from the group consisting of: substituted or unsubstituted with 1-20An alkyl group having carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulae 3-10 and formulae 3-11, Y5And Y6Each independently selected from CReAnd two ReLinked to form a 5-membered aromatic ring, a phenyl ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring.
According to an embodiment of the present invention, wherein, in formulae 3-6 to 3-13, X11-X14At least one or two of which are selected from CRx1，X21-X24At least one or two of which are selected from CRx2，X31-X34At least one or two of which are selected from CRx3，X41-X44At least one or two of which are selected from CRx4，X51-X54At least one or two of which are selected from CRx5And said R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms, or substituted or unsubstituted aryl having 2 to 20 carbon atomsSubstituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulae 3-6 to 3-13, X11-X14At least one or two of which are selected from CRx1，X21-X24At least one or two of which are selected from CRx2，X31-X34At least one or two of which are selected from CRx3，X41-X44At least one or two of which are selected from CRx4，X51-X54At least one or two of which are selected from CRx5And said R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulas 3-6 to 3-13, X12And/or X14Selected from the group consisting of CRx1，X22And/or X24Selected from the group consisting of CRx2，X32And/or X34Selected from the group consisting of CRx3，X42And/or X44Selected from the group consisting of CRx4，X52And/or X54Selected from the group consisting of CRx5And said R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted aryl havingA heteroaryl group of 3 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulas 3-6 to 3-13, X12And/or X14Selected from the group consisting of CRx1，X22And/or X24Selected from the group consisting of CRx2，X32And/or X34Selected from the group consisting of CRx3，X42And/or X44Selected from the group consisting of CRx4，X52And/or X54Selected from the group consisting of CRx5And said R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulas 3-6 to 3-13, X12And X14Each independently selected from CRx1，X22And X24Each independently selected from CRx2，X32And X34Each independently selected from CRx3，X42And X44Each independently selected from CRx4，X52And X54Each independently selected from CRx5(ii) a The R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, and combinations thereof.
According to an embodiment of the present invention, wherein, in the second compound, the LaEach occurrence being selected identically or differently from La-1To La-387The group consisting ofa-1To La-387See claim 22 for specific structure of (a).
According to an embodiment of the present invention, wherein, in the second compound, the LbHas a structure shown in formula 4:
Figure BDA0003043795300000271
R1to R7Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to an embodiment of the present invention, wherein in the second compound, the LbHas a structure shown as formula 4, wherein R1-R3At least one or two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least one or two of them are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or groups thereofAnd (6) mixing.
According to an embodiment of the present invention, wherein in the second compound, the LbHas a structure shown as a formula 4, wherein R1-R3At least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
According to an embodiment of the present invention, wherein, in the second compound, the LbEach occurrence being selected identically or differently from Lb1To Lb322The group consisting ofb1To Lb322See claim 24 for specific structure of (a).
According to one embodiment of the invention, wherein the second compound has Ir (L)a)2(Lb) In which LaEach occurrence being selected identically or differently from La-1To La-387Any one or any two of the group consisting of, LbIs selected from the group consisting of Lb1To Lb322Any one of the group consisting of.
According to an embodiment of the present invention, wherein the second compound is selected from the group consisting of compound 2-1 to compound 2-34, compound 2-39 to compound 2-70, compound 2-75 to compound 2-106, compound 2-111 to compound 2-142, compound 2-147 to compound 2-178, compound 2-183 to compound 2-214, compound 2-217 to compound 2-227, compound 2-229 to compound 2-241, compound 2-243 to compound 2-255, compound 2-257 to compound 2-269, compound 2-271 to compound 2-283, compound 2-285 to compound 2-297, compound 2-299 to compound 2-300, specific structures of the compound 2-1 to the compound 2-34, the compound 2-39 to the compound 2-70, the compound 2-75 to the compound 2-106, the compound 2-111 to the compound 2-142, the compound 2-147 to the compound 2-178, the compound 2-183 to the compound 2-214, the compound 2-217 to the compound 2-227, the compound 2-229 to the compound 2-241, the compound 2-243 to the compound 2-255, the compound 2-257 to the compound 2-269, the compound 2-271 to the compound 2-283, the compound 2-285 to the compound 2-297, and the compound 2-299 to the compound 2-300 are shown in claim 25.
According to an embodiment of the present invention, wherein the organic layer is a light emitting layer, the first compound is a host material, and the second compound is a light emitting material.
According to an embodiment of the invention, wherein the electroluminescent device emits red light.
According to an embodiment of the invention, wherein the electroluminescent device emits white light.
According to another embodiment of the present invention, there is also disclosed a display apparatus comprising an electroluminescent device. The specific structure of the electroluminescent device is shown in any one of the embodiments.
According to another embodiment of the present invention, there is also disclosed a combination of compounds comprising a first compound and a second compound;
the first compound has the structure of H-L-E;
h has a structure represented by formula 1:
Figure BDA0003043795300000281
in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rfthe same or different at each occurrence denotes mono-, poly-or no-substitution;
e has a structure represented by formula 2:
Figure BDA0003043795300000291
in formula 2, Z1To Z5At least one of which is N and the others are each independently selected from CRz；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R，Rfand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring;
the second compound is a metal complex having M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein M is selected from metals having a relative atomic mass greater than 40;
La、Lb、Lca first ligand, a second ligand and a third ligand which are respectively coordinated with the M; l isa、Lb、LcOptionally linked to form a multidentate ligand;
La、Lb、Lcmay be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of LaMay be the same or different; when n is 2, two LbMay be the same or different;
Lahas a structure as shown in formula 3:
Figure BDA0003043795300000292
wherein the content of the first and second substances,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring D and ring E via YaAnd YbFusing;
Yaand YbSelected from C or N, identically or differently at each occurrence;
Rd，Rethe same or different at each occurrence denotes mono-, poly-or unsubstituted;
X1-X4selected from CR, identically or differently at each occurrencexOr N;
Rd，Re，Rxeach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms-heteroaryl of 30 carbon atoms, substituted or unsubstituted alkylsilyl of 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl of 6 to 20 carbon atoms, substituted or unsubstituted amino of 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents Rd，Re，RxCan be optionally connected to form a ring;
Lband LcEach independently selected from any one of the following structures:
Figure BDA0003043795300000301
Ra，Rband RcThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xbselected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach independently selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atomsAn alkylsilyl group of carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
at LbAnd LcIn the structure (1), adjacent substituents Ra，Rb，Rc，RN1，RN2，RC1And RC2Can optionally be linked to form a ring;
and does not include the following: the first compound is
Figure BDA0003043795300000311
While the second compound is
Figure BDA0003043795300000312
In combination with other materials
The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161 of U.S. 2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.
Material synthesis:
the preparation method of the first compound and the second compound selected by the invention is not limited, and the following compounds are typically but not limited to exemplified, and the synthetic route and the preparation method thereof are as follows:
synthesis example 1: synthesis of Compound 1-1
Step 1: synthesis of intermediate 1
Figure BDA0003043795300000321
2-bromo-3-chloronitrobenzene (100g, 425.5mmol), 2-aminophenylboronic acid pinacol ester (102g, 468.1mmol), tetratriphenylphosphine palladium (4.9g, 4.25mmol), potassium carbonate (115g, 852mmol), toluene (1000mL), water (200mL) and ethanol (200mL) were added to a three-necked flask under nitrogen and reacted at 100 ℃ for 48 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and column chromatography purification (PE/EA ═ 4:1) gave intermediate 1(90g, yield: 85%) as a yellow oil.
Step 2: synthesis of intermediate 2
Figure BDA0003043795300000322
Intermediate 1(90g, 363mmol), acetonitrile (1000mL) were each placed in a three-necked flask and p-toluenesulfonic acid (193.2g, 1088mmol) was added portionwise at 0 ℃ and stirred for 30min, at which temperature an aqueous solution of a mixture of sodium nitrite (69g, 726mmol) and potassium iodide (150.6g, 907mmol) was slowly added dropwise. After the dropwise addition, the temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After completion of the reaction, a saturated aqueous solution of sodium thiosulfate was added dropwise to quench the reaction, the reaction mixture was concentrated and diluted with water, the mixed solution was extracted three times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent, and the mixture was subjected to column chromatography (PE/DCM ═ 10/1) to give intermediate 2(85g, yield: 65%) as a yellow solid.
And step 3: synthesis of intermediate 4
Figure BDA0003043795300000323
Intermediate 2(20g, 55.7mmol), intermediate 3(24.5g, 83.6mmol), tetrakistriphenylphosphine palladium (1.9g, 1.67mmol), potassium carbonate (15.4g, 111.4mmol), tetrahydrofuran (500mL), water (100mL), ethanol (100mL) were added to a three-necked flask under nitrogen and reacted at 70 ℃ for 48 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and purified by column chromatography (PE/EA ═ 4:1) to obtain intermediate 4(12g, yield: 55%) as a yellow solid.
And 4, step 4: synthesis of intermediate 5
Figure BDA0003043795300000324
Intermediate 4(12g, 30.15mmol), palladium acetate (338mg, 1.5mmol), tri-tert-butylphosphine (606mg, 3.0mmol), cesium carbonate (20g, 60.3mmol) and xylene (230mL) were added to a three-necked flask under nitrogen and reacted at 140 ℃ for 10 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and column chromatography purification (PE/EA ═ 6:1) gave intermediate 5(9g, yield: 80%) as a yellow solid.
And 5: synthesis of intermediate 6
Figure BDA0003043795300000331
Intermediate 5(9g, 24.9mmol), triphenylphosphine (19.6g, 74.7mmol) and o-dichlorobenzene (o-DCB) (100mL) were added to a three-necked flask under nitrogen and reacted at 200 ℃ for 12 h. After completion of the reaction, the solvent was removed by concentration, and the crude product was separated by column chromatography to give intermediate 6(7g, yield: 85%) as a yellow solid.1H NMR(400MHz,DMSO-d6)δ11.41(s,1H),8.20(d,J＝7.7Hz,1H),8.14(d,J＝8.4Hz,1H),8.03(d,J＝7.5Hz,1H),7.91(d,J＝7.8Hz,1H),7.58–7.46(m,2H),7.41(d,J＝7.9Hz,1H),7.39–7.31(m,4H),7.28(t,J＝7.7Hz,1H),7.15(d,J＝7.7Hz,1H)。
Step 6: synthesis of Compound 1-1
Figure BDA0003043795300000332
6(2g, 6.06mmol), 2(1.8g, 6.6mmol), cesium carbonate (3.9g, 12.12mmol) and DMF (60ml) were added to a three-necked flask under nitrogen and reacted at 80 ℃ for 5 h. After completion of the reaction, it was cooled to room temperature, distilled water was added, the solid was filtered, and the crude product was washed three times with (THF/Tol ═ 1:1) to give compound 1-1(2.4g, yield: 72%) as a yellow solid. The structure of this compound was confirmed to be the target product, molecular weight 561.2.
Synthesis example 2: synthesis of Compound 1-2
Step 1: synthesis of Compound 1-2
Figure BDA0003043795300000333
6(3g, 9.1mmol), 2(3.87g, 10mmol), palladium acetate (40mg, 0.02mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (147mg, 0.04mmol), cesium carbonate (5.9g, 18.2mmol) and xylene (100ml) were added to a three-necked flask under nitrogen protection and reacted at 140 ℃ for 10 hours. After the reaction was completed, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, concentrated to remove the solvent, and the crude product was washed with toluene, tetrahydrofuran, and acetone, respectively, to obtain compound 1-2(3g, yield: 51%) as a yellow solid. The structure of this compound was confirmed to be the target product, molecular weight 637.2.
It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and those skilled in the art can modify it to obtain the structures of other first compounds and second compounds selected by the present invention. Or may be obtained by referring to the chinese application with application numbers CN2020102702502 and CN2020102850167, which are not described herein again.
The method of fabricating the electroluminescent device is not limited, and the method of fabricating the following examples is only an example and should not be construed as limiting. The preparation of the following examples can be reasonably modified by those skilled in the art in light of the prior art. For example, the ratio of the materials in the light-emitting layer is not particularly limited, and those skilled in the art can reasonably select the ratio within a certain range according to the prior art, for example, the first compound accounts for 80% to 99%, the second compound accounts for 1% to 20% or preferably the second compound accounts for 1% to 10% of the total weight of the light-emitting layer materials.
Device example 1
First, cleaningA glass substrate with a 120nm thick Indium Tin Oxide (ITO) anode, then treated with UV ozone and oxygen plasma. After the treatment, the substrate was dried in a glove box filled with nitrogen gas to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees-8In the case of Torr
Figure BDA0003043795300000342
Figure BDA0003043795300000341
The rate of (a) was successively evaporated on the ITO anode by thermal vacuum. Compound HI was used as a Hole Injection Layer (HIL) with a thickness of
Figure BDA0003043795300000343
The compound HT is used as Hole Transport Layer (HTL) with a thickness of
Figure BDA0003043795300000347
Compound EB was used as an Electron Blocking Layer (EBL) with a thickness of
Figure BDA0003043795300000344
Then, the compound 1-1 as a host and the compound 2-2 as a dopant were co-evaporated to be used as an emission layer (EML) with a thickness of
Figure BDA0003043795300000345
The compound HB was used as a hole-blocking layer (HBL) with a thickness of
Figure BDA0003043795300000348
On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron-transporting layer (ETL) with a thickness of
Figure BDA0003043795300000349
Finally, evaporation
Figure BDA0003043795300000346
Thickness of 8-hydroxyquinoline-lithium (Liq) asElectron Injection Layer (EIL) and evaporation coating
Figure BDA00030437953000003410
As a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.
Device example 2
Device example 2 was implemented in the same manner as device example 1 except that compound 1-2 was used as a host in place of compound 1-1 in the light emitting layer (EML).
Device example 3
Device example 3 is the same as device example 1 except that compounds 2-125 are used as dopants in the light emitting layer (EML) instead of compound 2-2.
Device example 4
Device example 4 was implemented in the same manner as device example 2 except that compounds 2-125 were used as dopants in the light emitting layer (EML) instead of compound 2-2.
Device example 5
Device example 5 is the same as device example 2 except that compounds 2-43 are used as dopants in the light emitting layer (EML) instead of compound 2-2.
Device example 6
Device example 6 is the same as device example 2 except that compound 2-1 is used as a dopant instead of compound 2-2 in the light emitting layer (EML).
Device comparative example 1
Device comparative example 1 was conducted in the same manner as in device example 1 except that the compound RD-a was used as a dopant in the light emitting layer (EML) instead of the compound 2-2.
Device comparative example 2
Device comparative example 2 was conducted in the same manner as in device example 2 except that the compound RD-a was used as a dopant in the light emitting layer (EML) instead of the compound 2-2.
Device comparative example 3
Device comparative example 3 was implemented in the same manner as device example 1, except that compound CBP was used as a host instead of compound 1-1 in the light emitting layer (EML).
Device comparative example 4
Device comparative example 4 was the same as device comparative example 3 except that compound RD-a was used as a dopant instead of compound 2-2 in the light emitting layer (EML).
Device comparative example 5
The embodiment of device comparative example 5 is the same as device comparative example 3 except that compounds 2-43 are used as dopants in the light emitting layer (EML) instead of compound 2-2.
Device comparative example 6
The embodiment of device comparative example 6 is the same as device comparative example 3 except that compound 2-1 is used as a dopant instead of compound 2-2 in the light emitting layer (EML).
Device comparative example 8
Device comparative example 8 was the same as device example 5 except that compound a was used as a host in place of compound 1-2 in the light emitting layer (EML).
The device layer structures and thicknesses are shown in the table below. Wherein more than one of the materials used is obtained by doping different compounds in the recited weight ratios.
TABLE 1 device structures of device examples and comparative examples
Figure BDA0003043795300000351
Figure BDA0003043795300000361
The material structure used in the device is as follows:
Figure BDA0003043795300000362
Figure BDA0003043795300000371
table 2 shows the values at 15mA/cm2Under the conditions, the Voltage (Voltage, V), Power Efficiency (PE), and device lifetime (LT97) of device examples 1 to 6 and device comparative examples 1 to 6 and comparative example 8 were measured.
TABLE 2 device data
Figure BDA0003043795300000372
Figure BDA0003043795300000381
Discussion:
as shown in the table 2 below, the following examples,
the device experiment disclosed in the prior art (for example, patent KR1020150077220A) is referred to, and the host material (for example, compound CBP) commonly used in the prior art (for example, patent KR1020150077220A) and the host material compound a now commercially available, and the phosphorescent light-emitting material (for example, compound RD-a) commonly used in the prior art (for example, patent KR1020150077220A) are used as the compounds of the comparative examples.
From the device data we can find that: example 1 using the combination of the present invention (the first compound 1-1 and the second compound 2-2 as the light emitting layer) and comparative example 1 (the first compound 1-1 and RD-a as the light emitting layer), it was found that the voltages were consistent, but example 1 was unexpectedly improved in power efficiency and lifetime by 10lm/W (2.5 times) and 165 hours (41.3 times) respectively as compared with comparative example 1. Similarly, in example 2 using the combination of the present invention (the first compound 1-2 and the second compound 2-2 as the light emitting layer) and comparative example 2 (the first compound 1-2 and RD-a as the light emitting layer), it was found that example 2(3.4V) was 0.2V lower than comparative example 2(3.6V) in driving voltage, and example 2 was 11lm/W (2.0 times) and 1511 hour (116 times) higher in power efficiency and lifetime than comparative example 2, respectively, and a dramatic improvement was obtained, particularly, a lifetime was more than hundred times.
Example 3 using the combination of the present invention (the first compound 1-1 and the second compound 2-125 as the light-emitting layer) and comparative example 1 (the first compound 1-1 and RD-a as the light-emitting layer), it was found that the voltages were similar, but example 3 was 12lm/W (3.0 times) and 495.4 hours (123.9 times) higher in power efficiency and lifetime than comparative example 1, respectively, and similarly surprising improved.
Example 4 using the combination of the present invention (the first compounds 1 to 2 and the second compounds 2 to 125 as the light emitting layer) and comparative example 2 (the first compounds 1 to 2 and RD-a as the light emitting layer), it was found that the voltages were the same, but example 4 was 12lm/W (2.0 times) and 2056 hours (158.2 times) higher in power efficiency and lifetime than comparative example 1, respectively, and a very unexpected improvement was achieved, particularly, the lifetime was further improved up to 2069 hours.
These results show that the combination of the first compound and the second compound of the present invention can achieve a great improvement in device performance (driving voltage, power efficiency, and lifetime), and far surpass the device effect obtained when the first compound selected in the present invention is used and a phosphorescent light-emitting material in the prior art is used as a dopant, and illustrate the superiority of the combination of the first compound and the second compound of the present invention, and in particular, sufficiently demonstrate the unexpected effect brought by the use of the first compound selected in the present invention as a red phosphorescent host material in combination with the second compound having a specific structure.
Example 1 using the combination of the present invention (first compound 1-1 and second compound 2-2 as light emitting layers) and comparative example 3(CBP and 2-2 as light emitting layers), it was found that example 1(3.5V) was 5.1V lower than comparative example 3(8.6V) in terms of driving voltage, while example 1 was 10lm/W (2.5 times) and 162 hours (23.1 times) higher in power efficiency and lifetime than comparative example 3, respectively, and a very significant improvement was achieved.
Example 2 using the combination of the present invention (first compound 1-2 and second compound 2-2 as light emitting layers) and comparative example 3(CBP and 2-2 as light emitting layers), it was found that example 2(3.4V) was 5.2V lower than comparative example 3(8.6V) in terms of driving voltage, while example 1 was 13lm/W (3.3 times) and 1517 hours (216.7 times) higher in power efficiency and lifetime than comparative example 3, respectively, and that very significant improvements were achieved.
Example 5 using the combination of the present invention (first compounds 1-2 and second compounds 2-43 as light emitting layers) and comparative example 5(CBP and 2-43 as light emitting layers), it was found that example 5(3.6V) was lower by 4.6V than comparative example 5(8.2V) in terms of driving voltage, and that example 5 was higher by 21lm/W (2.6 times) and 867.6 hours (135.6 times) in power efficiency and lifetime than comparative example 5, respectively.
Example 6 using the combination of the present invention (first compound 1-2 and second compound 2-1 as light emitting layers) and comparative example 6(CBP and 2-1 as light emitting layers), it was found that example 6(3.5V) was 5.6V lower than comparative example 6(9.1V) in terms of driving voltage, and example 6 was 13lm/W (2.6 times) and 1215.8 hours (190 times) higher in power efficiency and lifetime, respectively, than comparative example 6.
These results show that the combination of the first compound and the second compound of the present invention can greatly improve the device performance, and far surpass the device effect obtained when the compound in the prior art is used as the host and the second compound selected by the present invention is used as the dopant, and show the superiority of the combination of the first compound and the second compound of the present invention, and particularly, the unexpected effect brought by the first compound selected by the present invention when used as the red phosphorescent host material in combination with the second compound having a specific structure is also fully demonstrated.
Example 5 using the combination of the present invention (the first compounds 1 to 2 and the second compounds 2 to 43 as the light-emitting layer), compared with comparative example 8 (the compounds a and 2 to 43 as the light-emitting layer) using the host material compound a which is now commercially available, it can be found that example 5(3.6V) is lower by 0.8V than comparative example 8(4.4V) in terms of driving voltage, and example 5 is higher by 2lm/W (7.4%) and 20 hours (2.3%) in power efficiency and lifetime, respectively, than comparative example 8. These data indicate that the disclosed material combinations can further improve device performance at levels that commercial materials have, which is very rare.
These results show that the combination of the first compound and the second compound of the present invention can greatly improve the device performance, and can further improve the level of the host material used in commercial applications, and further illustrate the superiority of the combination of the first compound and the second compound of the present invention, and in particular, fully demonstrate the unexpected effect brought by the combination of the first compound selected in the present invention as a red phosphorescent host material and the second compound having a specific structure.
In summary, the combination of the first compound and the second compound disclosed in the present invention can show excellent comprehensive device performance in devices, such as lower driving voltage, higher efficiency and ultra-long device lifetime, because the two compounds can be well matched with each other in terms of energy.
It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.

Claims (29)

1. An electroluminescent device, comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound;
the first compound has the structure of H-L-E;
h has a structure represented by formula 1:
Figure FDA0003043795290000011
in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rfthe same or different at each occurrence denotes mono-, poly-or no-substitution;
e has a structure represented by formula 2:
Figure FDA0003043795290000012
in formula 2, Z1To Z5At least one of which is N and the others are each independently selected from CRz；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R，Rfand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring;
the second compound is a metal complex having M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein M is selected from metals having a relative atomic mass greater than 40;
La、Lb、Lca first ligand, a second ligand and a third ligand which are respectively coordinated with the M; l isa、Lb、LcOptionally linked to form a multidentate ligand;
La、Lb、Lcmay be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of LaMay be the same or different; when n is 2, two LbMay be the same or different;
Lahas a structure as shown in formula 3:
Figure FDA0003043795290000021
wherein the content of the first and second substances,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring D and ring E via YaAnd YbFusing;
Yaand YbSelected from C or N, identically or differently at each occurrence;
Rd，Rethe same or different at each occurrence denotes mono-, poly-or unsubstituted;
X1-X4selected from CR, identically or differently at each occurrencexOr N;
Rd，Re，Rxeach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkylUnsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents Rd，Re，RxCan be optionally connected to form a ring;
Lband LcEach independently selected from any one of the following structures:
Figure FDA0003043795290000022
Ra，Rband RcThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xbselected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach independently selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groupAn unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
at LbAnd LcIn the structure (1), adjacent substituents Ra，Rb，Rc，RN1，RN2，RC1And RC2Can optionally be linked to form a ring;
and does not include the following: the first compound is
Figure FDA0003043795290000031
While the second compound is
Figure FDA0003043795290000032
2. The electroluminescent device of claim 1 wherein in said formula 1, ring a, ring B and ring C, identically or differently at each occurrence, are selected from aromatic rings having 6-18 carbon atoms, or heteroaromatic rings having 3-18 carbon atoms.
3. The electroluminescent device of claim 1 or 2, wherein the H has a structure represented by formula 1-a:
Figure FDA0003043795290000033
wherein A is1To A3Selected, identically or differently, on each occurrence from N or CR, F1To F10Selected identically or differently at each occurrenceself-CRfOr N;
R，Rfeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring;
preferably, RfEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, isocyano, hydroxyl, mercapto, and combinations thereof.
4. The electroluminescent device of any one of claims 1-3, wherein the H is selected from the group consisting of the following structures:
Figure FDA0003043795290000041
Figure FDA0003043795290000051
Figure FDA0003043795290000061
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
5. The electroluminescent device of any one of claims 1-4, wherein the E has a structure represented by any one of formulas 2-a through 2-h:
Figure FDA0003043795290000062
wherein Z is1To Z5Selected from CR, identically or differently at each occurrencez；
Wherein R iszEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 1 to 20 carbon atoms, or substituted or unsubstituted aryl having 2 to 30 carbon atomsSubstituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
preferably, RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof;
more preferably, RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, pyridyl, and combinations thereof.
6. An electroluminescent device as claimed in any one of claims 1 to 5 wherein the E is selected from substituted or unsubstituted triazinyl.
7. The electroluminescent device of any one of claims 1-6, wherein said E is selected from the group consisting of the following structures:
Figure FDA0003043795290000071
Figure FDA0003043795290000081
Figure FDA0003043795290000091
wherein in the above structure
Figure FDA0003043795290000092
Indicates the location of the structure attached to the L structure;
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
8. The electroluminescent device of any of claims 1-7, wherein in the first compound, the L is selected from a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;
preferably, said L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, phenanthrylene, and fluorenylene;
more preferably, said L is selected from the group consisting of the following structures:
Figure FDA0003043795290000093
wherein "+" in the above structure denotes a position where the structure is connected to the H structure,
Figure FDA0003043795290000101
indicates the location of attachment of the structure to the E structure;
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
9. The electroluminescent device of any one of claims 1-8, wherein the first compound is selected from the group consisting of compound 1-1 through compound 1-520, compound 1-1 through compound 1-520 having the structure of H-L-E, wherein H, L and E each correspond to a structure selected from the following table:
Figure FDA0003043795290000102
Figure FDA0003043795290000111
Figure FDA0003043795290000121
Figure FDA0003043795290000131
Figure FDA0003043795290000141
Figure FDA0003043795290000151
Figure FDA0003043795290000161
10. an electroluminescent device as claimed in any one of claims 1 to 9 wherein in the second compound, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; preferably, M is selected from Ir, Pt or Os; more preferably, M is Ir.
11. An electroluminescent device as claimed in any one of claims 1 to 10 wherein in the second compound, the LaHas a structure represented by any one of formulas 3-1 to 3-5:
Figure FDA0003043795290000162
wherein the content of the first and second substances,
ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
Rethe same or different at each occurrence denotes mono-, poly-or no-substitution;
X11-X14selected from CR, identically or differently at each occurrencex1Or N; x21-X24Selected from CR, identically or differently at each occurrencex2Or N; x31-X34Selected from CR, identically or differently at each occurrencex3Or N; x41-X44Selected from CR, identically or differently at each occurrencex4Or N; x51-X54Selected from CR, identically or differently at each occurrencex5Or N;
y is selected, identically or differently on each occurrence, from O, S, Se, NRd1，CRd1Rd1Or SiRd1Rd1(ii) a When two R are simultaneously presentd1When two R are presentd1May be the same or different; preferably, Y is selected, identically or differently on each occurrence, from O or S;
Y3and Y4Selected from CR, identically or differently at each occurrencedOr N;
Rx1、Rx2、Rx3、Rx4、Rx5、Rd1、Rdand ReEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted ammonia having 0 to 20 carbon atomsA group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
adjacent substituents Rx1、Rx2、Rx4、Rx5、Rd1、RdAnd ReCan optionally be linked to form a ring;
when R isx3Selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or substituted or unsubstituted amino groups having 0 to 20 carbon atoms, adjacent substituents Rx3Can optionally be linked to form a ring.
12. The electroluminescent device of any one of claims 1-10, wherein said LaHas a structure represented by any one of formulas 3-6 to 3-13:
Figure FDA0003043795290000171
wherein the content of the first and second substances,
X11-X14selected from CR, identically or differently at each occurrencex1Or N; x21-X24Selected from CR, identically or differently at each occurrencex2Or N; x31-X34Selected from CR, identically or differently at each occurrencex3Or N; x41-X44Selected from CR, identically or differently at each occurrencex4Or N; x51-X54Selected from CR, identically or differently at each occurrencex5Or N;
Y3and Y4Selected from CR, identically or differently at each occurrencedOr N;
Y5、Y6、Y7and Y8Selected from CR, identically or differently at each occurrenceeOr N;
y is selected, identically or differently on each occurrence, from O, S, Se, NRd1，CRd1Rd1Or SiRd1Rd1(ii) a When two R are simultaneously presentd1When two R are presentd1May be the same or different; preferably, Y is selected, identically or differently on each occurrence, from O or S;
Rx1、Rx2、Rx3、Rx4、Rx5、Rd1、Rdand ReEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rx1、Rx2、Rx4、Rx5、Rd1、RdAnd ReCan optionally be linked to form a ring;
when R isx3Selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstitutedWhen the substituent R is an unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms or a substituted or unsubstituted amino group having 0 to 20 carbon atoms, the adjacent substituents Rx3Can optionally be linked to form a ring.
13. The electroluminescent device as claimed in claim 12, wherein in formulae 3-6 to 3-11, Y is3-Y4Is N;
preferably, wherein in formulae 3-6, formulae 3-7, formulae 3-9, formulae 3-10, and formulae 3-11, Y4Is N; in the formulae 3 to 8Y3Is N.
14. The electroluminescent device as claimed in claim 12, wherein in formulae 3-6 to 3-13, Y is3And Y4Selected from CR, identically or differently at each occurrenced；Y5、Y6、Y7And Y8Selected from CR, identically or differently at each occurrencee。
15. The electroluminescent device as claimed in claim 12, wherein in formulae 3-6 to 3-13, Y is3And/or Y4Selected from the group consisting of CRdAnd said R isdEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a pharmaceutically acceptable salt thereofSubstituted or unsubstituted alkylsilyl groups of 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups of 6 to 20 carbon atoms, substituted or unsubstituted amino groups of 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
preferably, said R isdEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
16. An electroluminescent device as claimed in any one of claims 12 to 15 wherein in formulae 3-6 to 3-13, Y is5-Y8At least one or two of which are selected from CReAnd said R iseEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
preferably, said R iseEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
17. The electroluminescent device as claimed in claim 16, wherein in formulae 3-6 and formulae 3-9, Y is6Selected from the group consisting of CRe(ii) a In the formulae 3 to 8, Y4Selected from the group consisting of CRdAnd/or Y6-Y8At least one of which is selected from CRe(ii) a In formulae 3-10 and 3-11, Y5And Y6At least one of which is CRe；
And said R isd，ReEach occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
preferably, said R isd，ReIdentical in each occurrence orVariously selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
18. The electroluminescent device as claimed in claim 16, wherein in formulae 3 to 10 and formulae 3 to 11, Y is5And Y6At least one of which is selected from CReAnd said R iseEach occurrence, identically or differently, is selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
preferably, Y5And Y6Each independently selected from CReAnd two ReLinked to form a 5-membered aromatic ring, a phenyl ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring.
19. An electroluminescent device as claimed in any one of claims 12 to 18 wherein in formulae 3-6 to 3-13, X11-X14At least one or two of which are selected from CRx1，X21-X24At least one or two of which are selected from CRx2，X31-X34At least one or two of which are selected from CRx3，X41-X44At least one or two of which are selected from CRx4，X51-X54At least one or two of which are selected from CRx5And said R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
preferably, said R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
20. The electroluminescent device as claimed in claim 19, wherein in formulae 3-6 to 3-13, X12And/or X14Selected from the group consisting of CRx1，X22And/or X24Selected from the group consisting of CRx2，X32And/or X34Selected from the group consisting of CRx3，X42And/or X44Selected from the group consisting of CRx4，X52And/or X54Selected from the group consisting of CRx5And said R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof;
preferably, Rx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and combinations thereof.
21. The electroluminescent device as claimed in claim 20, wherein in formulae 3-6 to 3-13, X12And X14Each independently selected from CRx1，X22And X24Each independently selected from CRx2，X32And X34Each independently selected from CRx3，X42And X44Each independently selected from CRx4，X52And X54Each independently selected from CRx5(ii) a The R isx1、Rx2、Rx3、Rx4、Rx5Each occurrence, identically or differently, is selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, and combinations thereof.
22. The electroluminescent device of claim 1, wherein said LaEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0003043795290000201
Figure FDA0003043795290000211
Figure FDA0003043795290000221
Figure FDA0003043795290000231
Figure FDA0003043795290000241
Figure FDA0003043795290000251
Figure FDA0003043795290000261
Figure FDA0003043795290000271
Figure FDA0003043795290000281
Figure FDA0003043795290000291
Figure FDA0003043795290000301
Figure FDA0003043795290000311
Figure FDA0003043795290000321
Figure FDA0003043795290000331
Figure FDA0003043795290000341
Figure FDA0003043795290000351
Figure FDA0003043795290000361
Figure FDA0003043795290000371
Figure FDA0003043795290000381
Figure FDA0003043795290000391
Figure FDA0003043795290000401
Figure FDA0003043795290000411
Figure FDA0003043795290000421
Figure FDA0003043795290000431
Figure FDA0003043795290000441
Figure FDA0003043795290000451
Figure FDA0003043795290000461
Figure FDA0003043795290000471
Figure FDA0003043795290000481
23. a method as claimed in any one of claims 1 to 22The electroluminescent device of, wherein LbHas a structure shown in formula 4:
Figure FDA0003043795290000482
wherein R is1To R7Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
preferably, wherein R1-R3At least one or two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least one or two of which are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof;
more preferably, R1-R3At least two of which are the same or different at each occurrenceIs selected from the group consisting of substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
24. The electroluminescent device of claim 23, wherein said LbEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0003043795290000483
Figure FDA0003043795290000491
Figure FDA0003043795290000501
Figure FDA0003043795290000511
Figure FDA0003043795290000521
Figure FDA0003043795290000531
Figure FDA0003043795290000541
Figure FDA0003043795290000551
25. the electroluminescent device of any one of claims 1-24, wherein the second compound has Ir (L)a)2(Lb) In which LaEach occurrence being selected identically or differently from La-1To La-387Any one or any two of the group consisting of, LbIs selected from the group consisting of Lb1To Lb322Any one of the group consisting of;
preferably, the second compound is selected from the group consisting of compound 2-1 to compound 2-34, compound 2-39 to compound 2-70, compound 2-75 to compound 2-106, compound 2-111 to compound 2-142, compound 2-147 to compound 2-178, compound 2-183 to compound 2-214, compound 2-217 to compound 2-227, compound 2-229 to compound 2-241, compound 2-243 to compound 2-255, compound 2-257 to compound 2-269, compound 2-271 to compound 2-283, compound 2-285 to compound 2-297, compound 2-299 to compound 2-300;
wherein the compound 2-1 to the compound 2-34, the compound 2-39 to the compound 2-70, the compound 2-75 to the compound 2-106, the compound 2-111 to the compound 2-142, the compound 2-147 to the compound 2-178, the compound 2-183 to the compound 2-214 have Ir (L)a)2(Lb) Wherein two L areaSame, LaAnd LbEach corresponding to a structure selected from those listed in the following table:
Figure FDA0003043795290000552
Figure FDA0003043795290000561
Figure FDA0003043795290000571
wherein, the compound 2-217 to the compound 2-227, the compound 2-229 to the compound 2-241, the compound 2-243 to the compound 2-255, the compound 2-257 to the compound 2-269, the compound 2-271 to the compound 2-283, the compound 2-285 to the compound 2-297, the compound 2-299 to the compound 2-300 have Ir (L)a)2(Lb) Wherein two L areaDifferent, LaAnd LbRespectively corresponding to the structures listed in the following table:
Figure FDA0003043795290000572
Figure FDA0003043795290000581
26. the electroluminescent device of any one of claims 1-25, wherein the organic layer is a light emitting layer, the first compound is a host material, and the second compound is a light emitting material.
27. The electroluminescent device of claim 26, wherein the device emits red or white light.
28. A display assembly comprising an electroluminescent device as claimed in any one of claims 1 to 27.
29. A combination of compounds comprising a first compound and a second compound;
the first compound has the structure of H-L-E;
h has a structure represented by formula 1:
Figure FDA0003043795290000582
in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rfthe same or different at each occurrence denotes mono-, poly-or no-substitution;
e has a structure represented by formula 2:
Figure FDA0003043795290000591
in formula 2, Z1To Z5At least one of which is N and the others are each independently selected from CRz；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R，Rfand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted with 6-20 carbonsAn arylsilyl group of atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents R, RfCan optionally be linked to form a ring;
the second compound is a metal complex having M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein M is selected from metals having a relative atomic mass greater than 40;
La、Lb、Lca first ligand, a second ligand and a third ligand which are respectively coordinated with the M; l isa、Lb、LcOptionally linked to form a multidentate ligand;
La、Lb、Lcmay be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of LaMay be the same or different; when n is 2, two LbMay be the same or different;
Lahas a structure as shown in formula 3:
Figure FDA0003043795290000592
wherein the content of the first and second substances,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring E is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring D and ring E via YaAnd YbFusing;
Yaand YbSelected from C or N, identically or differently at each occurrence;
Rd，Rethe same or different at each occurrence denotes mono-, poly-or unsubstituted;
X1-X4at each occurrenceAre identically or differently selected from CRxOr N;
Rd，Re，Rxeach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rd，Re，RxCan be optionally connected to form a ring;
Lband LcEach independently selected from any one of the following structures:
Figure FDA0003043795290000601
Ra，Rband RcThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xbselected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach independently selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
at LbAnd LcIn the structure (1), adjacent substituents Ra，Rb，Rc，RN1，RN2，RC1And RC2Can optionally be linked to form a ring;
and does not include the following: the first compound is
Figure FDA0003043795290000602
While the second compound is
Figure FDA0003043795290000603
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