Organic electroluminescent material and device

Abstract

The present invention relates to an organic electroluminescent material and device. When the organic electroluminescent material is used in OLED, especially in a blue light emitting region, it exhibits enhanced phosphorescence quantum yield, good luminescence stability, and high luminescence efficiency, and is suitable for use as an emitter material in OLED applications. The organic electroluminescent material of the present invention can obtain an organic electroluminescent device with deep blue phosphorescence electroluminescence and improved luminescence efficiency, and the luminescent device has good thermal stability. The organic electroluminescent material of the present invention regulates its photophysical properties by regulating the structure of ligands surrounding a metal center and regulating the structure of substituents on the ligands, and has the advantages of a narrow emission spectrum, high stability, and high efficiency, and has broad application prospects in many fields of OLED displays and lighting lamps.

Description

Technical Field

[0001] The invention belongs to the technical field of luminescent materials, and in particular relates to an organic electroluminescent material and device. Background Art

[0002] Optoelectronic devices utilizing organic materials are becoming increasingly popular for a variety of reasons. Many materials used to make the devices are relatively inexpensive, so organic optoelectronic devices have the potential to have cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) can make them more suitable for specific applications, such as manufacturing on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.

[0003] OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly attractive technology for use in applications such as flat panel displays, lighting, and backlighting.

[0004] One application of phosphorescent emitting molecules is full-color displays. Industry standards for such displays require pixels that are suitable for emitting specific colors. Specifically, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. In conventional liquid crystal displays, an absorption filter is used to filter the emission from a white backlight to produce red, green, and blue emissions. The same technology can also be used for OLEDs. White OLEDs can be single-emission layer (EML) devices or stacked structures. Color can be measured using CIE coordinates well known in the art, and existing luminescent materials have the disadvantages of poor stability and low luminous efficiency.

[0005] In view of the above reasons, the present invention is proposed. Summary of the invention

[0006] In order to solve the above problems existing in the prior art, the present invention provides an organic electroluminescent material, application and consumer product. When the organic electroluminescent material is used in OLED, especially in the blue light emission region, it exhibits enhanced phosphorescence quantum yield and is suitable for use as a light-emitting layer material in OLED applications.

[0007] The first object of the present invention is to provide an organic electroluminescent material, which has good electroluminescent stability and excellent luminescent efficiency.

[0008] The second object of the present invention is to provide a use of the organic electroluminescent material in an organic electroluminescent device.

[0009] The third object of the present invention is to provide a consumer product comprising the organic electroluminescent material.

[0010] In order to achieve the above object, the present invention adopts the following technical solution:

[0011] An organic electroluminescent material, comprising any one of the metal complexes represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), formula (7) or formula (8):

[0012]

[0013]

[0014] Among them, X 1 , X 2 , X 3 are each independently selected from C or N;

[0015] T is selected from O, S, CR'R", NR 0 or T is replaced by R' and R";

[0016] Y is selected from a single bond, O or S;

[0017] M is selected from Be, Mg, Al, Ca, Ti, Mn, Co, Cu, Zn, Ga, Ge, Zr, Ru, Rh, Ag, Re, Au, Pt or Pd;

[0018] R 0 , R', R", R 1 ~R 18 Each independently selected from hydrogen, deuterium, a halogen atom, a nitrile group, a C1-C 40 Straight chain alkyl with C1~C 40 Straight chain heteroalkyl with C3~C 40 A branched or cyclic alkyl group having C1 to C 40 Alkoxy with C6~C 60 Arylalkyl, having C6~C 60 Aryloxy, with C6~C 60 Aromatic amino groups with C3~C 40 Silane groups with C2~C 40 Alkenyl, with C4~C 40 Cycloalkenyl, having C2~C 40 heteroalkenyl, having C2~C 40 Alkenyl or alkynyl, having C6~C 60 Aromatic or aromatic ring system, with C2~C 60 A group consisting of a heteroaromatic or heteroaromatic ring system, R 1~R 16 Two or more adjacent substituent groups in may be optionally joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

[0019] Further, the M is selected from Al, Cu, Au, Pt or Pd; T is selected from O, S, CR'R", NR 0 ; Y is selected from a single bond or O.

[0020] Furthermore, the R 0 , R', R", R 1 ~R 18 Each independently selected from hydrogen, deuterium, fluorine, nitrile, C1-C 40 Straight chain alkyl with C1~C 40 Straight chain heteroalkyl with C3~C 40 A branched or cyclic alkyl group having C1 to C 40 Alkoxy with C6~C 60 Arylalkyl, having C6~C 60 Aryloxy, with C6~C 60 Aromatic amino groups with C3~C 40 Silane groups with C6~C 60 Aromatic or aromatic ring system, with C2~C 60 A group consisting of a heteroaromatic or heteroaromatic ring system, R 0 , R', R", R 1 ~R 18 Two or more adjacent substituent groups in may be optionally joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.

[0021] Aromatic or heteroaromatic ring systems in the sense of the present invention are intended to be taken to mean systems which do not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be linked by non-aromatic units, such as C, N, O or S atoms. Thus, for example, systems such as fluorene, 9,9′-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers etc. are also taken to mean aromatic ring systems in the sense of the present invention, as are systems in which two or more aryl groups are linked, for example, by short alkyl groups.

[0022] An aryl group in the sense of the present invention contains 5 to 60 carbon atoms, a heteroaryl group in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatoms are preferably selected from N, O or S. An aryl or heteroaryl group is taken here to mean a simple aromatic ring, i.e. benzene, naphthalene etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene etc., or a fused aryl or heteroaryl group, such as anthracene, phenanthrene, quinoline, isoquinoline etc. Aromatic rings which are linked to one another by single bonds, such as biphenyl, are in contrast not referred to as aryl or heteroaryl groups, but as aromatic ring systems.

[0023] Alkyl in the sense of the present invention contains 1 to 40 carbon atoms and straight-chain or branched alkyl radicals in which individual hydrogen atoms or -CH2- groups may also be substituted, alkenyl or alkynyl radicals containing at least two carbon atoms, and, by way of non-limiting example, alkyl, alkenyl or alkynyl radicals are preferably taken to mean the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0024] Alkoxy is preferably taken to mean alkoxy having 1 to 40 carbon atoms, methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.

[0025] Heteroalkyl is preferably an alkyl radical having 1 to 40 carbon atoms and is taken to mean a radical in which individual hydrogen atoms or -CH2- groups are replaced by oxygen, sulfur or halogen atoms and is taken to mean an alkoxy radical, an alkylthio radical, a fluorinated alkoxy radical, a fluorinated alkylthio radical, in particular a methoxy radical, an ethoxy radical, an n-propoxy radical, an isopropoxy radical, an n-butoxy radical, an isobutoxy radical, a sec-butoxy radical, a tert-butoxy radical, a methylthio radical, an ethylthio radical, an n-propylthio radical, an isopropylthio radical, an n-butylthio radical, an isobutylthio radical, a sec-butylthio radical, a tert-butylthio radical, a trifluoromethylthio radical, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.

[0026] Generally speaking, the cycloalkyl and cycloalkenyl groups according to the present invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more -CH2- groups may be replaced by the above groups; in addition, one or more hydrogen atoms may also be replaced by a deuterium atom, a halogen atom or a nitrile group.

[0027] The aromatic or heteroaromatic radicals according to the invention may in each case also be replaced by the above-mentioned radicals R 0 Substituted aromatic or heteroaromatic ring systems are particularly those derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, trimerized indene, isotrimerized indene, spirotrimerized indene, spiroistrimerized indene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline , isoquinoline, acridine, phenanthridine, benzo[5,6]quinoline, benzo[6,7]quinoline, benzo[7,8]quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthimidazole, pyridimidazole, pyrazinimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthimidazole, anthraoxazole, phenanthromoxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzene pyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescein ring, naphthyridine, azacarbazole, benzocarboline, carboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, quinazoline, indolizine and benzothiadiazole or radicals derived from combinations of these systems.

[0028] Furthermore, the R 0 , R 1 ~R 18 R', R" are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, R A1 ~RA55 , R B1 ~R B45 , R C1 ~R C295 The group composed of;

[0029] Among them, R A1 ~R A55 The structural formula shown is as follows:

[0030]

[0031]

[0032] R B1 ~R B45 The structure shown is as follows:

[0033]

[0034]

[0035] R C1 ~R C295 The structure shown is as follows:

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042] Furthermore, the R 0 , R', R", R 1 ~R 18 Each is independently selected from the group consisting of hydrogen, fluorine, nitrile, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl and biphenyl.

[0043] Furthermore, the metal complex comprises one of PT1 to PT300:

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055] An application of the organic electroluminescent material in an organic electroluminescent device.

[0056] The organic electroluminescent device of the present invention can obtain blue light with high luminous efficiency.

[0057] Furthermore, the organic electroluminescent device comprises an anode, a cathode and at least one organic layer disposed between the anode and the cathode, and the organic layer comprises the organic electroluminescent material of the present invention.

[0058] Furthermore, the organic layer also includes a main material, and the main material is selected from the group consisting of the following chemical groups: triphenylene, carbazole, indolecarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolecarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene and aza-(5,9-diaza-13b-boronaphtho[3,2,1-de]anthracene).

[0059] The organic layer of the present invention may be a light-emitting layer and the organic electroluminescent material as described herein may be a light-emitting layer dopant or a non-light-emitting layer dopant.

[0060] Furthermore, the organic layer may further comprise a host and a dopant, wherein the dopant comprises the organic electroluminescent material.

[0061] The organic electroluminescent material may be a sensitizer; wherein the device may further comprise an acceptor, a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0062] The organic electroluminescent device of the present invention may further comprise a light-emitting region, wherein the light-emitting region contains a compound as disclosed in the above compound section of the present disclosure.

[0063] Furthermore, the main material is selected from the group consisting of the following structures:

[0064]

[0065] The materials described herein as being suitable for use in a particular layer in an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the light-emitting layer dopants disclosed herein can be used in combination with a wide variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0066] These processes are generally known to those skilled in the art and they can apply them without inventive step to organic electroluminescent devices comprising the compounds according to the invention.

[0067] According to one embodiment, novel ligands for metal complexes are disclosed. The inventors have discovered that the introduction of these ligands unexpectedly narrows the emission spectrum, lowers the sublimation temperature, and improves the luminescence efficiency of the device.

[0068] As the preparation method of the organic electroluminescent device of the present invention, the following preparation method can be listed, but it is not limited thereto, and those skilled in the art can make various changes according to the technical common sense in the field. The above-mentioned preparation method includes the following steps:

[0069] Cleaning process: Use cleaning agent, deionized water, organic solvent, etc. to clean the glass substrate with ITO;

[0070] A step of forming a hole injection layer: depositing a hole injection layer forming material containing the organic electroluminescent material of the present invention on the aforementioned anode layer by vacuum deposition, thereby forming a hole injection layer containing the organic electroluminescent material of the present invention on the aforementioned substrate;

[0071] A step of forming a hole transport layer: forming a hole transport layer on the hole injection layer by vacuum evaporation;

[0072] A step of forming an organic light-emitting layer: vacuum-depositing an organic light-emitting layer-forming material containing the material of the present invention on the aforementioned hole transport layer to form an organic light-emitting layer containing the organic electroluminescent material of the present invention on the aforementioned hole transport layer;

[0073] A step of forming an electron transport layer: vacuum evaporating an electron transport layer forming material containing the organic electroluminescent material of the present invention on the aforementioned organic light-emitting layer, thereby forming an electron transport layer containing the organic electroluminescent material of the present invention on the aforementioned organic light-emitting layer;

[0074] Step of forming a cathode layer: forming a cathode layer by evaporating, sputtering or spin coating a cathode forming material on the electron transport layer.

[0075] A consumer product comprising the organic electroluminescent device.

[0076] The consumer product of the present invention can be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, light therapy devices, and signage.

[0077] Compared with the prior art, the present invention has the following beneficial effects:

[0078] (1) When the organic electroluminescent material of the present invention is used in OLED, especially in the blue light emitting region, it exhibits enhanced phosphorescence quantum yield, good luminescence stability, and high luminescence efficiency, and is suitable for use as an emitter material in OLED applications. The organic electroluminescent material of the present invention can obtain an organic electroluminescent device with blue phosphorescent electroluminescence and improved luminescence efficiency, and the luminescent device has good thermal stability. The consumer product of the present invention can obtain an electronic device with blue phosphorescent electroluminescence and improved luminescence efficiency by containing the organic electroluminescent device of the present invention;

[0079] (2) The organic electroluminescent material described in the present invention regulates its photophysical properties by adjusting the structure of the ligands surrounding the metal center and the structure of the substituents on the ligands. It has the advantages of narrow emission spectrum, high stability and high efficiency, and has broad application prospects in many fields of OLED displays and lighting. BRIEF DESCRIPTION OF THE DRAWINGS

[0080] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0081] Figure 1 A schematic diagram of an organic light-emitting device 100 is shown. The illustration is not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, an electron transport layer 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL) 110. The device 100 may be manufactured by depositing the described layers in order.

[0082] Figure 2 Schematic diagram of an organic light-emitting device 200 showing two light-emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 can be prepared by depositing the described layers in sequence. Because the most common OLED device has one light-emitting layer, and the device 200 has a first light-emitting layer and a second light-emitting layer, the light emission peaks of the first light-emitting layer and the second light-emitting layer can be overlapping, cross-overlapping, or non-overlapping. In the corresponding layers of the device 200, materials similar to those described with respect to the device 100 can be used. Figure 2 One example is provided of how some layers may be added from the structure of device 100 . DETAILED DESCRIPTION

[0083] To make the purpose, technical solution and advantages of the present invention clearer, the technical solution of the present invention will be described in detail below. Obviously, the described embodiments are only part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other implementation methods obtained by ordinary technicians in this field without creative work belong to the scope of protection of the present invention.

[0084] The "EQE" in the present invention refers to the external quantum efficiency of a device, that is, the ratio of the number of photons emitted by the device to the number of electrons injected into the device.

[0085] The organic electroluminescent device described in the present invention comprises at least one organic layer disposed between an anode and a cathode and electrically connected to the anode and the cathode. Figure 1A schematic diagram of an organic light-emitting device 100 is shown. The illustration is not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, an electron transport layer 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL) 110. The device 100 may be manufactured by depositing the described layers in order.

[0086] Figure 2 A schematic diagram of an organic light-emitting device 200 containing two light-emitting layers is shown. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 can be prepared by depositing the layers described in sequence. Because the most common OLED device has a single-color light-emitting layer or a light-emitting layer having three primary colors, the device 200 has two light-emitting layers of the same light color. In the corresponding layers of the device 200, materials similar to those described with respect to the device 100 can be used. Figure 2 One example is provided of how some layers may be added from the structure of device 100 .

[0087] Figure 1 and Figure 2 The simple layered structure illustrated in is provided as a non-limiting example, and it should be understood that embodiments of the present invention can be used in conjunction with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be achieved by combining the various layers described in different ways, or several layers can be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials different from those specifically described may be used. Although many of the examples provided herein describe various layers as including a single material, it will be understood that combinations of materials, such as a mixture of a matrix and a dopant, or more generally, a mixture, can be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 204 transports holes and injects holes into light-emitting layer 205, and may be described as a hole transport layer or an electron blocking layer. In one embodiment, the OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may include a single layer or may further include, for example, Figure 1 and Figure 2 Multiple layers of different organic materials are described.

[0088] Structures and materials not specifically described may also be used, such as PLEDs comprising polymer materials. As another example, an OLED having a single organic layer or multiple stacks may be used. The OLED structure may be separated from Figure 1 and Figure 2 For example, the substrate may include angled reflective surfaces to improve light coupling.

[0089] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, organic vapor deposition methods, or applying one or more layers with the aid of carrier gas sublimation, wherein the deposition temperature is between 10 and 20 °C. 5 The material is applied at a pressure between 100 mbar and 1 bar. A particular example of this method is an organic vapor jet printing method, in which the material is applied directly through a nozzle and is therefore structured. Other suitable deposition methods include, for example, producing one or more layers by spin coating, or by means of any desired printing method such as screen printing, flexographic printing, lithography, photoinduced thermography, thermal transfer, inkjet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. In addition, hybrid methods are feasible, in which, for example, one or more layers are applied from a solution and one or more additional layers are applied by vapor deposition.

[0090] The device manufactured according to the embodiment of the present invention may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrode and the organic layer from being damaged by exposure to harmful substances in the environment, including moisture, vapor and / or gas, etc. The barrier layer may be deposited on the substrate, the electrode, under the substrate, the electrode, or next to the substrate, the electrode, or on any other part of the device, including the edge. The barrier layer may include a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include a composition having a single phase and a composition having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic or organic compound or both. Preferably, the barrier layer includes a mixture of a polymeric material and a non-polymeric material. In order to be regarded as a mixture, the aforementioned polymer and non-polymeric materials constituting the barrier layer should be deposited under the same conditions and / or at the same time. The weight ratio of the polymeric material to the non-polymeric material may be in the range of 95 / 5 to 5 / 95. In one example, the mixture of the polymeric material and the non-polymeric material is essentially composed of polymeric silicon and inorganic silicon.

[0091] In any of the above-mentioned compounds used in each layer of the above-mentioned OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specific listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, etc., may be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (such as (but not limited to) alkyl, aryl, cycloalkyl, heteroaryl, etc.) may also be in their non-deuterated, partially deuterated, and fully deuterated forms.

[0092] The materials and structures described herein can be applied in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can use the materials and structures.

[0093] Furthermore, organic devices such as organic transistors may use the materials and structures.

[0094] In the following examples of the present invention, conventional preparation methods are used unless otherwise specified. The raw materials used can be obtained from public commercial channels unless otherwise specified, and the percentages are by mass unless otherwise specified.

[0095] In order to explain the present invention more clearly, the technical solution of the present invention is described below in conjunction with some specific embodiments:

[0096] In the embodiments of the present invention, the performance testing conditions of the prepared electroluminescent device are as follows:

[0097] Chromaticity coordinates: tested using a spectrum scanner PhotoResearch PR-715;

[0098] Current-voltage: Tested using a digital source meter Keithley 2420;

[0099] Power efficiency: tested using NEWPORT 1931-C;

[0100] Brightness: Tested using a brightness meter Minolta CS-1000A.

[0101] Example 1

[0102] The preparation method of the metal complex PT32 comprises the following steps:

[0103] Step 1: Preparation of compound Int-1

[0104]

[0105] 20.0mmol of 1-bromo-8-tert-butyl-dibenzofuran (reactant 1) was dissolved in 20mL of dry toluene and 20mL of triethylamine, and then 22.0mmol of S2 (reactant 2), 2.0mmol of cuprous iodide, and 2.0mmol of PdCl2(PPh3)2 were added. The temperature was raised to reflux and stirred for reaction for 24 hours, then cooled to room temperature, 100mL of water was added, and the reaction was stirred for 30 minutes. The reaction was extracted with ethyl acetate, and the organic phase was collected, dried, filtered, and the filtrate was concentrated to dryness. The intermediate Int-1 was obtained as a yellow solid with a yield of 76%.

[0106] Step 2: Preparation of compound Int-2

[0107]

[0108] Under nitrogen protection, 20.0 mmol of Int-1 was dissolved in 60 mL of dichloromethane, 2.0 mmol of trifluoromethanesulfonic acid was added, and the reaction was stirred at room temperature for 15 hours. 20 mL of saturated sodium bicarbonate aqueous solution was added and stirred for 1 hour. The organic phase was separated, dried, filtered, and concentrated under reduced pressure. The residue was separated and purified by silica gel column to obtain compound Int-2 as a white solid with a yield of 77%.

[0109] Step 3: Preparation of compound Int-3

[0110]

[0111] Under nitrogen protection, 20.0 mmol of Int-2 was dissolved in 50 mL of glacial acetic acid, and 7.7 mmol of potassium iodate and 13.1 mmol of potassium iodide were added. The temperature was raised to reflux and stirred for reaction for 2 hours, then cooled to room temperature, filtered, and the filter cake was washed with water and saturated sodium bisulfite aqueous solution. The filter cake was separated and purified by silica gel column to obtain white solid Int-3 with a yield of 92%.

[0112] Step 4: Preparation of compound Int-4

[0113]

[0114] Under nitrogen protection, 20.0 mmol of Int-3 was dissolved in 60 mL of toluene, and 22.0 mmol of benzimidazole, 60.0 mmol of anhydrous potassium carbonate, 2.0 mmol of cuprous iodide and 60.0 mmol of N, N'-dimethylethylenediamine were added. The temperature was raised to reflux and stirred for reaction for 24 hours, then cooled to room temperature, filtered, and the filter cake was washed with dichloromethane, concentrated under reduced pressure, and purified by silica gel column to obtain white solid Int-4 with a yield of 83%.

[0115] Step 5: Preparation of compound Int-5

[0116]

[0117] Under nitrogen protection, 20.0 mmol of Int-4 was dissolved in 60 mL of dichloromethane, cooled to 0°C, 30.0 mmol of boron tribromide was added dropwise, the temperature was raised to room temperature and stirred for reaction for 12 hours, 100 mL of 5% aqueous sodium hydroxide solution was added dropwise, the organic phase was separated, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure, separated and purified by silica gel column to obtain yellow solid Int-5 with a yield of 93%.

[0118] Step 6: Preparation of compound Int-6

[0119]

[0120] Under nitrogen protection, 20.0 mmol of Int-5 was dissolved in 50 mL of DMF, and 44.0 mmol of (3,5-di-tert-butylphenyl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate and 0.8 mmol of anhydrous copper acetate were added. The temperature was raised to reflux and stirred for reaction for 2 hours, then cooled to room temperature and filtered. The filtrate was poured into 200 mL of ice water and filtered. The filter cake was washed with water and separated and purified by silica gel column to obtain white solid Int-6 with a yield of 76%.

[0121] Step 7: Preparation of metal complex PT32

[0122]

[0123] Under nitrogen protection, 15.0 mmol of Int-6 was dissolved in 400 mL of DMF, 15.0 mmol of Pt(COD)Cl2 and 45.0 mmol of sodium acetate were added, stirred and heated to reflux for 15 hours, cooled to room temperature, concentrated under reduced pressure, extracted with dichloromethane, collected organic phase, washed with water, dried, filtered, the filtrate was concentrated under reduced pressure, separated and purified by silica gel column to obtain compound PT32 as a yellow solid with a yield of 56%. HRMS (MALDI): calculated value: 1026.4412, found value: 1026.4504.

[0124] Referring to the above-mentioned similar synthesis method, metal complexes: PT01~PT31, PT33~PT42 were prepared.

[0125] Example 2

[0126] The preparation of the metal complex PT87 comprises the following steps:

[0127] Step 1: Preparation of compound Int-8

[0128]

[0129] Referring to the synthesis method of the first step of Example 1, only the compound S2 in the first step of Example 1 was replaced by trimethylsilyl acetylene to prepare compound Int-8 with a yield of 82%.

[0130] Step 2: Preparation of compound Int-9

[0131]

[0132] Under nitrogen protection, 10.0 mmol of Int-8 was dissolved in 40 mL of dichloromethane, cooled to 0°C, 11.0 mmol of NIS was added in batches, the temperature was raised to room temperature and stirred for 2 hours, 50 mL of water was added, extracted with dichloromethane, the organic phase was collected and dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column to obtain compound Int-9 with a yield of 91%.

[0133] Step 3: Preparation of compound Int-10

[0134]

[0135] Under nitrogen protection, 20.0 mmol of Int-9 was dissolved in 80 mL of nitromethane and 20 mL of THF, and 60.0 mmol of copper bromide and 10.0 mmol of anhydrous potassium phosphate were added. The reaction was stirred at room temperature for 12 hours, and the mixture was concentrated to dryness under reduced pressure. The residue was separated and purified by silica gel column to obtain compound Int-10 as a white solid with a yield of 79%.

[0136] Step 4: Preparation of compound Int-11

[0137]

[0138] Under nitrogen protection, 10.0 mmol of Int-10 was dissolved in 60 mL of THF, and 11.0 mmol of (3-(4-tert-butylpyridin-2-yl)phenyl)boric acid, 20.0 mmol of anhydrous sodium carbonate, 0.1 mmol of Pd(PPh3)4 and 20 mL of water were added. The reaction was stirred at room temperature for 12 hours, 50 mL of water was added, and the mixture was extracted with ethyl acetate. The organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure. The compound Int-11 was separated and purified by silica gel column to obtain a yield of 86%.

[0139] Step 5: Preparation of compound Int-12

[0140]

[0141] 10.0 mmol of the intermediate Int-11 was dissolved in 40 mL of THF and 10 mL of triethylamine, 0.5 g of 10% palladium / carbon was added, hydrogen was introduced to 0.1 MPa, and the reaction was stirred at room temperature for 12 hours. The reaction was filtered, the filter cake was washed with THF, the filtrate was concentrated under reduced pressure, separated and purified by silica gel column, and then recrystallized from toluene / ethanol to obtain a yellow solid Int-12 with a yield of 100%.

[0142] Step 6: Preparation of compound Int-13

[0143]

[0144] Under nitrogen protection, 10.0 mmol of Int-12 was dissolved in 40 mL of dichloromethane, 12.0 mmol of iodine chloride was added, and the reaction was stirred at room temperature for 12 hours. 50 mL of saturated aqueous sodium bisulfite solution was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure. The compound Int-13 was separated and purified using a silica gel column to obtain a yield of 89%.

[0145] Step 7: Preparation of Compound Int-14

[0146]

[0147] Referring to the synthesis method of the fourth step of Example 1, only the compound Int-3 in the fourth step of Example 1 was replaced by Int-13 to prepare compound Int-14 with a yield of 83%.

[0148] Step 8: Preparation of Compound Int-15

[0149]

[0150] Referring to the synthesis method of the sixth step of Example 1, only the compound Int-5 in the sixth step of Example 1 was replaced by Int-14 to prepare compound Int-15 with a yield of 82%.

[0151] Step 9: Preparation of metal complex PT87

[0152]

[0153] Under nitrogen protection, 5.0 mmol of Int-15 was dissolved in 40 mL of glacial acetic acid, and 5.0 mmol of potassium tetrachloroplatinate was added. The temperature was raised to reflux with stirring for 24 hours, then the mixture was cooled to room temperature, concentrated to dryness under reduced pressure, and separated and purified by silica gel column to obtain compound PT87 with a yield of 35%. HRMS (MALDI): calculated value: 954.3836, found value: 955.3932.

[0154] Referring to the above-mentioned similar synthesis method, metal complexes: PT43~PT86, PT88~PT169 were prepared.

[0155] Example 3

[0156] The preparation of the metal complex PT181 comprises the following steps:

[0157] Step 1: Preparation of compound Int-16

[0158]

[0159] Referring to the synthesis method of the fourth step of Example 1, only Int-3 in the fourth step of Example 1 was replaced by S3. After separation and purification by silica gel column, yellow solid Int-16 was prepared with a yield of 87%.

[0160] Step 2: Preparation of compound Int-17

[0161]

[0162] Under nitrogen protection, 10.0 mmol of Int-16 was dissolved in 40 mL of DMF, and 12.0 mmol of bipyralidin, 15.0 mmol of anhydrous potassium acetate, 0.1 mmol of PdCl2(dppf)CH2C12 and 0.1 mmol of cuprous iodide were added. The temperature was raised to 100 °C and stirred for 12 hours. The temperature was cooled to room temperature, 150 mL of ice-water solution was added, and the mixture was filtered. The filter cake was washed with water and separated and purified by silica gel column to obtain compound Int-17 as a white solid with a yield of 87%.

[0163] Step 3: Preparation of compound Int-18

[0164]

[0165] Under nitrogen protection, 12.0 mmol of Int-17 was dissolved in 40 mL of toluene, 20 mL of ethanol and 20 mL of water, and 10.0 mmol of 9-(6-bromopyridin-2-yl)-9H-carbazole, 36.0 mmol of anhydrous potassium carbonate and 0.01 mmol of Pd0132 were added. The temperature was raised to reflux and stirred for reaction for 12 hours, then cooled to room temperature, 50 mL of water was added, extracted with ethyl acetate, the organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column to obtain compound Int-18 as a white solid with a yield of 86%.

[0166] Step 4: Preparation of compound Int-19

[0167]

[0168] Referring to the synthesis method of the sixth step of Example 1, only the compound Int-5 in the sixth step of Example 1 was replaced by Int-18 to prepare compound Int-19 with a yield of 78%.

[0169] Step 5: Preparation of metal complex PT181

[0170]

[0171] Referring to the synthesis method of the ninth step of Example 2, only Int-15 in the ninth step of Example 2 was replaced by Int-19. After separation and purification by silica gel column, yellow solid PT181 was prepared with a yield of 46%. HRMS (MALDI): calculated value: 917.3057, found value: 919.3073.

[0172] Example 4

[0173] The preparation of the metal complex PT221 comprises the following steps:

[0174] Step 1: Preparation of compound Int-20

[0175]

[0176] Referring to the synthesis method of Example 1, only S2 in the first step of Example 1 was replaced by S5 to prepare compound Int-20 with a yield of 84%.

[0177] Step 2: Preparation of compound Int-21

[0178]

[0179] Referring to the synthesis method of Example 1, only Int-1 in the second step of Example 1 was replaced by Int-20 to prepare compound Int-21 with a yield of 74%.

[0180] Step 3: Preparation of compound Int-22

[0181]

[0182] Referring to the synthesis method of Example 1, only Int-2 in the third step of Example 1 was replaced by Int-21 to prepare compound Int-22 with a yield of 98%.

[0183] Step 4: Preparation of compound Int-23

[0184]

[0185] Under nitrogen protection, 20.0 mmol of Int-22 was dissolved in 60 mL of toluene, and 22.0 mmol of benzimidazole, 60.0 mmol of anhydrous potassium carbonate, 2.0 mmol of cuprous iodide and 40.0 mmol of N, N'-dimethylethylenediamine were added. The temperature was raised to reflux and stirred for reaction for 24 hours, then cooled to room temperature, filtered, and the filter cake was washed with dichloromethane, concentrated under reduced pressure, and purified by silica gel column to obtain white solid Int-23 with a yield of 86%.

[0186] Step 5: Preparation of compound Int-24

[0187]

[0188] Under nitrogen protection, 22.0 mmol of 65% potassium hydroxide was dissolved in 40 mL of DMSO, 22.0 mmol of carbazole was added, and the reaction was stirred for 30 minutes. 20.0 mmol of Int-23 was added, and the temperature was raised to 85°C and stirred for 15 hours. The temperature was cooled to room temperature, and the reaction solution was poured into 200 mL of ice water and filtered. The filter cake was washed with water and ethanol, and separated and purified by silica gel column to obtain yellow solid Int-24 with a yield of 87%.

[0189] Step 6: Preparation of compound Int-25

[0190]

[0191] Referring to the synthesis method of the sixth step of Example 1, only the compound Int-5 in the sixth step of Example 1 was replaced by Int-24 to prepare compound Int-25 with a yield of 80%.

[0192] Step 7: Preparation of metal complex PT221

[0193]

[0194] Referring to the synthesis method of the ninth step of Example 2, only Int-15 in the ninth step of Example 2 was replaced by Int-25. After separation and purification by silica gel column, yellow solid PT221 was prepared with a yield of 45%. HRMS (MALDI): calculated value: 987.3476, found value: 988.3568.

[0195] The metal complexes: PT170-PT180, PT182-PT220, PT222-PT237 were prepared by using a similar synthesis method as in Examples 3 and 4.

[0196] Example 5

[0197] Preparation of metal complex PT253:

[0198]

[0199] 0.40 mmol of ligand S7, 0.45 mmol of potassium tetrachloroplatinite and 0.04 mmol of tetrabutylammonium bromide were dispersed in 30 mL of acetic acid. Under nitrogen protection, the mixture was heated to reflux with stirring for 20 hours. The mixture was cooled to room temperature, filtered, and the solid was washed with water and acetone. The solid was separated and purified by silica gel column to obtain compound PT253 as a yellow solid with a yield of 30%. HRMS (MALDI): calculated value: 753.2683, found value: 754.2779.

[0200] Example 6

[0201] The preparation of the metal complex PT264 comprises the following steps:

[0202] Step 1: Preparation of compound Int-26

[0203]

[0204] Referring to the synthesis method of the first to third steps in Example 4, only the 2-chloro-6-ethynylpyridine in the first step of Example 4 was replaced by 2-methyl-6-ethynylpyridine to prepare compound Int-26.

[0205] Step 2: Preparation of compound Int-27

[0206]

[0207] Under nitrogen protection, 12.0 mmol of (3-(1H-benzo[d]imidazol-1-yl)phenyl)boric acid was dissolved in 40 mL of toluene, 20 mL of ethanol and 20 mL of water, and 10.0 mmol of Int-26, 36.0 mmol of anhydrous sodium carbonate and 0.01 mmol of Pd(PPh3)4 were added. The temperature was raised to reflux and stirred for reaction for 12 hours, then cooled to room temperature, 50 mL of water was added, and the mixture was extracted with ethyl acetate. The organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column to obtain compound Int-27 as a yellow solid with a yield of 92%.

[0208] Step 3: Preparation of compound Int-28

[0209]

[0210] Referring to the synthesis method of the sixth step of Example 1, only the compound Int-5 in the sixth step of Example 1 was replaced by Int-27 to prepare compound Int-28 with a yield of 79%.

[0211] Step 4: Preparation of metal complex PT264

[0212]

[0213] Referring to the synthesis method of the ninth step of Example 2, only Int-15 in the ninth step of Example 2 was replaced by Int-28. After separation and purification by silica gel column, yellow solid PT264 was prepared with a yield of 42%. HRMS (MALDI): calculated value: 912.3367, found value: 914.3385.

[0214] Referring to the synthesis method similar to that of the above-mentioned Examples 5 and 6, metal complexes: PT238-PT252, PT254-PT263, PT265-PT276 were prepared.

[0215] Example 7

[0216] The preparation of the metal complex PT292 comprises the following steps:

[0217] Step 1: Preparation of compound Int-29

[0218]

[0219] Referring to the synthesis method of the first to third steps in Example 4, only S1 is replaced by s8, and the 2-chloro-6-ethynylpyridine in the first step of Example 4 is replaced by m-chlorophenylacetylene to prepare compound Int-29.

[0220] Step 2: Preparation of compound Int-30

[0221]

[0222] Under nitrogen protection, 10.0 mmol of Int-29 was dissolved in 50 mL of dry THF, cooled to -78°C, and 12.0 mmol of 2.5 M n-butyl lithium n-hexane solution was added dropwise. The reaction was stirred for 10 minutes, and 15.0 mmol of trimethyl borate was added dropwise. The temperature was warmed to room temperature and stirred for 1 hour. 20 mL of 2 M dilute hydrochloric acid aqueous solution was added, and the mixture was extracted with ethyl acetate. The organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness. It was dispersed with n-hexane, filtered, and the filter cake was washed with n-hexane to obtain compound Int-30 as a white solid with a yield of 82%.

[0223] Step 3: Preparation of compound Int-31

[0224]

[0225] Under nitrogen protection, 10.0 mmol of Int-30 was dissolved in 40 mL of toluene, 20 mL of ethanol and 20 mL of water, and 12.0 mmol of 2-methyl-6-bromopyridine, 36.0 mmol of anhydrous sodium carbonate and 0.02 mmol of Pd(PPh3)4 were added. The temperature was raised to reflux and stirred for reaction for 12 hours, then cooled to room temperature, 50 mL of water was added, extracted with ethyl acetate, the organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column to obtain compound Int-31 as a yellow solid with a yield of 76%.

[0226] Step 4: Preparation of compound Int-32

[0227]

[0228] Under nitrogen protection, 10.0 mmol of Int-31 was dissolved in 40 mL of toluene, and 12.0 mmol of benzimidazole, 15.0 mmol of sodium tert-butoxide, 0.01 mmol of Pd2(dba)3 and 0.02 mmol of Xantphos were added. The temperature was raised to 100°C and stirred for reaction for 12 hours. The temperature was cooled to room temperature, 50 mL of water was added, and the mixture was extracted with ethyl acetate. The organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure. The compound Int-32 was separated and purified by silica gel column to obtain a yellow solid with a yield of 88%.

[0229] Step 5: Preparation of compound Int-33

[0230]

[0231] Referring to the synthesis method of the sixth step of Example 1, only the compound Int-5 in the sixth step of Example 1 was replaced by Int-32 to prepare compound Int-33 with a yield of 84%.

[0232] Step 6: Preparation of metal complex PT292

[0233]

[0234] Referring to the synthesis method of the ninth step of Example 2, only Int-15 in the ninth step of Example 2 was replaced by Int-33. After separation and purification by silica gel column, yellow solid PT292 was prepared with a yield of 40%. HRMS (MALDI): calculated value: 928.3138, found value: 929.3232.

[0235] Referring to the above-mentioned similar synthesis method, metal complexes: PT277~PT291, PT293~PT300 were prepared.

[0236] Preparation of organic electroluminescent devices

[0237] The glass substrate with patterned ITO electrodes was ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in an acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with a UV cleaner for 10 minutes, and bombarded with a low-energy cation beam.

[0238] Place the treated ITO glass substrate in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -3 Pa, and silver is evaporated on the above ITO film as an anode, and the thickness of the evaporated film is Continue to evaporate the compound HATCN as a hole injection layer, and the evaporated film thickness is HTM is further evaporated on the hole injection layer to form a hole transport layer with a thickness of

[0239] BPrime was evaporated on the hole transport layer as an electron blocking layer with a film thickness of

[0240] On the electron blocking layer, metal complex and PH020 are evaporated as the organic light-emitting layer of the device, wherein PH020 is the main material and the metal complex is the doping material, the doping concentration is 10%, and the evaporated film thickness is

[0241] A layer of LiQ and ET318 is further evaporated on the organic light-emitting layer as the electron transport layer of the device, wherein LiQ is 50% of the mass of ET318 and the thickness of the evaporated film is

[0242] A layer of LiF is continuously evaporated on the above electron transport layer as the electron injection layer of the device, and the evaporated film thickness is

[0243] On the electron injection layer, magnesium and silver are evaporated as the cathode layer of the device, wherein the mass ratio of magnesium to silver is 1:10 and the thickness of the evaporated film is

[0244] Finally, the compound NPP is evaporated on the cathode layer as a capping layer, and the thickness of the evaporated film is To prepare the organic electroluminescent element of the present invention, Figure 1 device 100.

[0245] Comparative Example 1

[0246] The compound shown in BD010 was used to replace the metal complex of the organic electroluminescent device, and the other steps were the same as above to prepare a comparative element 1.

[0247] The structural formulas of the aforementioned HATCN, HTM, BPrime, PH020, BD010, NPP, and ET318 are as follows:

[0248]

[0249] Example 8

[0250] According to the same steps as the preparation of the above-mentioned organic electroluminescent device, the metal complex contained in the organic electroluminescent material of the present invention is used to replace the metal complex of the above-mentioned organic electroluminescent device to manufacture organic electroluminescent elements PT-1 to PT-25, and the driving voltage and current efficiency of the light-emitting elements PT-1 to PT-25 and the organic electroluminescent element prepared in Comparative Example 1 and the life of the element are measured using a digital source meter and a brightness meter. Specifically, the voltage is increased at a rate of 0.1 V per second, and the current density of the organic electroluminescent element is measured when it reaches 10 mA / cm 2 The voltage at this time is the driving voltage, and the brightness at this time is measured at the same time; the ratio of brightness to current density is the current efficiency; the LT95% life test is as follows: use a brightness meter at 1000cd / m 2 At the same brightness, the current is kept constant and the brightness decay of the organic electroluminescent element is measured to be 950cd / m 2 The time is in hours, and some of the results are summarized in Table 1. *The data are normalized compared to the comparative element 1.

[0251] Table 1

[0252]

[0253] It can be seen from Table 1 that, compared with the comparative element 1, the organic electroluminescent element prepared by the metal complex of the present invention has a lower driving voltage, a higher external quantum emission efficiency and an improved half-peak width, and a better color purity, and is an organic electroluminescent material with excellent performance.

[0254] The metal complex BD010 of the comparative element 1 is distinguished from the metal complex of the present invention in that the ligand of the metal complex of the present invention uses a phenanthrene derivative as the parent core, has strong planar conjugation ability and good stability, while the ligand of the metal complex BD010 uses oxygen as a bridging group to connect the two fragments of carbazole and imidazole, the planar conjugation is segmented, the conjugation ability is weak, the ligand freely rotates around oxygen as the center, causing energy loss, and the stability of the metal complex is reduced. The metal complex of the present invention uses phenanthrene as the plane to anchor the two fragments of imidazole and carbazole or pyridine, has a more stable structure, and is more conducive to electron transport and molecular film formation. Therefore, the element performance is better than that of the comparative element.

[0255] The above is only a specific embodiment of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art can easily think of changes or substitutions within the technical scope disclosed by the present invention, which should be included in the protection scope of the present invention. Therefore, the protection scope of the present invention should be based on the protection scope of the claims.

Claims

1. An organic electroluminescent material, It is characterized in that The organic electroluminescent material comprises one of the following structures:

2. Use of the organic electroluminescent material according to claim 1 in an organic electroluminescent device.

3. The use according to claim 2, It is characterized in that The organic electroluminescent device comprises an anode, a cathode and at least one organic layer disposed between the anode and the cathode, and the organic layer comprises the organic electroluminescent material according to claim 1.

4. The use according to claim 3, It is characterized in that The organic layer further comprises a main material, and the main material is selected from the group consisting of the following structures:

5. A consumer product comprising the organic electroluminescent device according to any one of claims 2 to 4.

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