Metal complex, organic electroluminescent element and consumer product

Abstract

The invention discloses a metal complex, an organic electroluminescent element and a consumer product. The metal complex provided by the invention comprises a ligand LA with a structure shown in the following formula. When the metal complex is applied to the organic electroluminescent element, excellent element performance can be obtained, especially the service life of the element is prolonged, the efficiency of the element is improved, and the metal complex has wide application prospects in the fields of OLED display, illumination and the like. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of luminescent materials, and particularly relates to a metal complex, an organic electroluminescent device, and a consumer product. Background Art

[0002] Currently, optoelectronic devices using organic materials have become increasingly popular, and many of the materials used to fabricate such devices are relatively inexpensive. Therefore, organic optoelectronic devices have the potential for cost advantages over inorganic devices. Additionally, the inherent properties of organic materials (such as their flexibility) can make them more suitable for specific applications, such as fabrication 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 an organic thin film that emits light when a voltage is applied to the device. OLEDs are becoming an increasingly attractive technology for applications such as flat panel displays, lighting, and backlighting.

[0004] One application of phosphorescent emission molecules is full-color displays. Industry standards for such displays require pixels 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, absorption filters are used to filter the emission from a white backlight to produce red, green, and blue emissions. The same technique 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. The luminescent materials in the prior art have poor luminescence stability and low luminescence efficiency.

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

[0006] In order to solve the above problems existing in the prior art, the present invention provides a metal complex, as well as an organic electroluminescent device and a consumer product containing the metal complex. When the metal complex of the present invention is used in an OLED, especially when used in the green emission region, it exhibits an enhanced phosphorescence quantum yield.

[0007] In a first aspect, the present invention provides a metal complex, the metal complex comprising a ligand represented by formula LA:

[0008]

[0009] Wherein, W is selected from O, S, or NR 3 ;

[0010] X1 to X 4 each independently selected from N or CR 4 ;

[0011] R 1 to R 4 is the same or different at each occurrence and is selected from hydrogen or the group consisting of: deuterium, a halogen atom, a nitrile group, an acyl group, a carboxylic acid, an ether, an ester group, an isonitrile group, a sulfide group, a selenoalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, a substituted or unsubstituted C 1 to C 40 linear alkyl, a substituted or unsubstituted C 1 to C 40 linear heteroalkyl, a substituted or unsubstituted C 3 to C 40 branched or cyclic alkyl, a substituted or unsubstituted C 3 to C 40 branched or cyclic heteroalkyl, a substituted or unsubstituted C 1 to C 40 linear alkoxy, a substituted or unsubstituted C 3 to C 40 branched or cyclic alkoxy, a substituted or unsubstituted C 6 to C 60 arylalkyl, a substituted or unsubstituted C 6 to C 60 aryloxy, a substituted or unsubstituted C 6 to C 60 arylamino, a substituted or unsubstituted C 3 to C 40 silyl, a substituted or unsubstituted C 2 to C 40 alkenyl, a substituted or unsubstituted C 4 to C 40 cycloalkenyl, a substituted or unsubstituted C 2 to C 40 heteroalkenyl, a substituted or unsubstituted C 2 to C 40 alkynyl, a substituted or unsubstituted C 6 to C 60 aryl, a substituted or unsubstituted C 2 to C 60 heteroaryl, and any two or more adjacent R 1 to R 4 may optionally be joined or fused to form a substituted or unsubstituted ring. Optionally, when substituted, the substituent is selected from deuterium, a halogen atom, a nitrile group, a hydroxyl group, a C 1 -C 6 linear alkyl, a C 3 -C 6 branched alkyl, a C1 -C 6 a straight-chain alkoxy or C 3 -C 6 a branched-chain alkoxy;

[0012] represents a single bond or a double bond, and when represents a double bond, R 3 does not exist;

[0013] the ligand LA coordinates via the metal M to form a five-membered chelate ring;

[0014] M is capable of coordinating with other ligands; and the ligand LA is capable of connecting with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand;

[0015] the M is selected from one of Os, Ir, Pd, Pt, Cu, Ag and Au.

[0016] In some embodiments, the M is selected from Ir, Pd or Pt.

[0017] In some embodiments, the chemical formula of the metal complex is M(LA) m (LB) n (LC) r , wherein, each occurrence of M is independently selected from Pt or Ir;

[0018] LA, LB and LC are the first ligand, the second ligand and the third ligand coordinating with the metal M respectively, and LC and LB are the same or different; LA, LB and LC can optionally connect to form a multidentate ligand;

[0019] m is 1, 2 or 3, n is 0, 1 or 2, r is 0, 1 or 2, and m + n + r is equal to the oxidation state of the metal M.

[0020] In some embodiments, when m is greater than or equal to 2, the multiple LAs are the same or different. In some embodiments, when n is equal to 2, the two LBs are the same or different. In some embodiments, when r is equal to 2, the two LCs are the same or different.

[0021] In some embodiments, each occurrence of the LB, LC is independently selected from any one of the following structures:

[0022]

[0023] wherein, Y 1 ~Y 11 are each independently selected from N or CR 14 , and T 1 is selected from BR 12 , NR12 、PR 12 、O, S, Se, C=O, S=O, SO 2 、CR 12 R 13 、SiR 12 R 13 and GeR 12 R 13 from one of them, R 12 and R 13 can be joined or fused arbitrarily to form a ring;

[0024] R 11 、R 12 、R 13 、R 14 are each independently selected from hydrogen or the group consisting of: deuterium, fluorine, nitrile group, substituted or unsubstituted C 1 ~C 40 linear alkyl, substituted or unsubstituted C 1 ~C 40 linear heteroalkyl, substituted or unsubstituted C 3 ~C 40 branched or cyclic alkyl, substituted or unsubstituted C 3 ~C 40 branched or cyclic heteroalkyl, substituted or unsubstituted C 3 ~C 40 silyl, substituted or unsubstituted C 6 ~C 60 aryl, substituted or unsubstituted C 2 ~C 60 heteroaryl group, optionally, when the above substitution, the substituent is selected from deuterium, halogen atom, nitrile group, hydroxyl group, C 1 -C 6 linear alkyl, C 3 -C 6 branched alkyl, C 1 -C 6 linear alkoxy or C 3 -C 6 branched alkoxy.

[0025] In some embodiments, the metal complex has the chemical formula Ir(LA) m (LB) n , m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, and m + n = 3; when m is 1, the two LBs are the same or different; when m is 2 or 3, the multiple LAs are the same or different, where LA and LB have the definitions described in the present invention.

[0026] In some embodiments, the chemical formula of the metal complex is Ir(LA)(LB)2 , Ir(LA) 2 (LB) or Ir(LA) 3 , where LA and LB have the definitions described in the present invention.

[0027] In some embodiments, LB is selected from the group consisting of LB1 - LB432:

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] Optionally, some or all of the hydrogen atoms in LB can be replaced by deuterium atoms.

[0040] In some embodiments, the metal complex includes a ligand LA represented by the following formula:

[0041]

[0042] Wherein, R 1 and R 2 are the same or different and are each independently selected from hydrogen, deuterium, cyano group, halogen atom, C1 - C6 alkyl without substituents, halogenated C1 - C6 alkyl, C6 - C10 aryl without substituents, C6 - C10 aryl substituted by C1 - C4 alkyl, C3 - C8 heteroaryl without substituents, C3 - C8 cycloalkyl without substituents. Optionally, R 1 and R 2 combine with the carbon atom to which they are attached to form C3 - C8 cycloalkyl or C6 - C20 aryl;

[0043] Z 1 -Z 4 each group is independently selected from CH or N;

[0044] q is 0, 1, 2 or 3, and each R aa is independently selected from hydrogen, deuterium, cyano group, halogen atom, C1-C6 alkyl without substituents, halogenated C1-C6 alkyl, C6-C10 aryl without substituents, C6-C10 aryl substituted by C1-C4 alkyl, C3-C20 heteroaryl without substituents, C3-C8 cycloalkyl without substituents. Optionally, when q is 2 or 3, adjacent R aa combines with the carbon atom to which it is attached to form C3-C8 cycloalkyl or C6-C2 aryl.

[0045] In some embodiments, R 1 and R 2 are selected from the following groups: hydrogen, fluorine, chlorine, bromine, cyano group, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, phenyl substituted by methyl, phenyl, pyridyl, cyclopentyl, or R 1 and R 2 combine with the carbon atom to which they are attached to form cyclopentyl, cyclohexyl,

[0046] In some embodiments, each R aa is selected from the following groups: hydrogen, fluorine, chlorine, bromine, cyano group, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, phenyl substituted by methyl, phenyl, pyridyl, carbazolyl, or adjacent R aa combines with the carbon atom to which it is attached to form cyclopentyl, cyclohexyl,

[0047] In the present invention represents the fused joint.

[0048] In some embodiments, the metal complex has the structure shown in formula (I):

[0049]

[0050] wherein, m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, and m + n = 3; when m is 1, two LBs are the same or different; when m is 2 or 3, multiple LAs are the same or different; W, X1 to X4 have the definitions in the present invention;

[0051] R a ~R h are the same or different each time they appear and are selected from hydrogen or a group consisting of the following: deuterium, halogen atom, cyano group, acyl group, carboxylic acid, ether, ester group, isocyano group, sulfide group, selenoalkyl group, sulfinyl group, sulfonyl group, phosphino group, substituted or unsubstituted C 1 ~C 40Straight-chain alkyl, substituted or unsubstituted C 1 ~C 40 Straight-chain heteroalkyl, substituted or unsubstituted C 3 ~C 40 Branched or cyclic alkyl, substituted or unsubstituted C 3 ~C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C 1 ~C 40 Straight-chain alkoxy, substituted or unsubstituted C 3 ~C 40 Branched or cyclic alkoxy, substituted or unsubstituted C 6 ~C 60 Arylalkyl, substituted or unsubstituted C 6 ~C 60 Aryloxy, substituted or unsubstituted C 6 ~C 60 Arylamino, substituted or unsubstituted C 3 ~C 40 Silyl, substituted or unsubstituted C 2 ~C 40 Alkenyl, substituted or unsubstituted C 4 ~C 40 Cycloalkenyl, substituted or unsubstituted C 2 ~C 40 Heteroalkenyl, substituted or unsubstituted C 2 ~C 40 Alkynyl, substituted or unsubstituted C 6 ~C 60 Aryl, substituted or unsubstituted C 2 ~C 60 A group consisting of heteroaryl, and any two or more adjacent substituents can optionally be joined or fused to form a substituted or unsubstituted ring. Optionally, the substituents during the above substitution are selected from deuterium, halogen atoms, nitrile groups, hydroxyl groups, C 1 -C 6 Straight-chain alkyl, C 3 -C 6 Branched-chain alkyl, C 1 -C 6 Straight-chain alkoxy or C 3 -C 6 Branched-chain alkoxy.

[0052] In some embodiments, the R 1 ~R 4 、R a ~R h Each independently is selected from the group consisting of hydrogen, deuterium, fluorine, nitrile groups, R A1 ~R A55 、R B1 ~R B45, R C1 ~R C295 form a group;

[0053] wherein, said R A1 ~R A55 has the following structural formula:

[0054]

[0055]

[0056] R B1 ~R B45 has the following structural formula:

[0057]

[0058]

[0059] R C1 ~R C295 has the following structural formula:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] R A1 -R A55 , R B1 -R B45 and R C1 -R C295 some or all of the hydrogen atoms therein may be replaced by deuterium atoms.

[0067] In some embodiments, R a , R c , R d , R e , R f and R h are the same or different and are each independently selected from hydrogen, deuterium, a halogen atom, a nitrile group, an unsubstituted C1-C4 alkyl group, a deuterated C1-C4 alkyl group. Preferably, R a , R c , R d , R e , R f and Rh are the same, both being hydrogen or deuterium.

[0068] In some embodiments, R b and R g are the same or different and are each independently selected from hydrogen, deuterium, a halogen atom, a nitrile group, an unsubstituted C1-C4 alkyl group, a deuterated C1-C4 alkyl group. Preferably, R b and R g are the same, both being hydrogen, deuterium, methyl, ethyl or trideuteromethyl.

[0069] In some embodiments, W is selected from N.

[0070] In some embodiments, the LA is selected from the group consisting of LA1-LA176:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] Optionally, some or all of the hydrogen atoms in LA1-LA176 may be replaced by deuterium atoms.

[0078] Furthermore, the metal complex has the chemical formula Ir(LAi) 2 (LBj), Ir(LAi)(LBj) 2 , or Ir(LAi) 3 ;

[0079] where i is an integer from 1 to 176 and j is an integer from 1 to 432, and LA1-LA176 and LB1-LB432 have the same meanings as described above.

[0080] The organic electroluminescent material of the present invention includes one or more of the metal complexes of the present invention. The organic electroluminescent material of the present invention may be formed only by one or more of the metal complexes of the present invention, or may contain other materials in addition to the metal complexes of the present invention.

[0081] By including the aforementioned metal complex in the organic electroluminescent material of the present invention, an organic electroluminescent material with green, yellow or red electroluminescence and high luminous efficiency can be obtained. In addition, the organic electroluminescent material of the present invention is an organic electroluminescent material with good thermal stability.

[0082] In a second aspect, the present invention provides an organic electroluminescent device, which includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, and the organic layer includes the metal complex.

[0083] In some embodiments, the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron transport layer. The light emitting layer includes a host material and a dopant material, and the dopant material includes the metal complex.

[0084] In some embodiments, the host material mainly includes the group consisting of the following compounds: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, and azadibenzoselenophene, indolocarbazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, azaindolocarbazole, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene) and their derivatives or combinations.

[0085] Optionally, any substituent in the host material is independently a non-fused substituent selected from the group consisting of C n H 2n+1 、OC n H 2n+1 、OAr 1 、N(C n H 2n+1 ) 2 、N(Ar 1 )(Ar 2 )、CH=CH-C n H 2n+1 、C≡CC n H 2n+1 、Ar 1 、Ar 1 -Ar 2 、C n H 2n -Ar 1 or unsubstituted, where n is an integer from 1 to 10; and where Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and their heteroaromatic analogs.

[0086] In some embodiments, the host material is selected from any one compound, two compounds, or a combination of multiple compounds shown below:

[0087]

[0088]

[0089] In some embodiments, the mass ratio of the host material to the doping material is 99:1 to 1:99.

[0090] In some embodiments, the mass percentage of the doping material in the light-emitting layer is 1% to 50%, preferably 1% to 10%.

[0091] In the organic electroluminescent device of the present invention, one layer may be a layer containing the metal complex of the present invention, or two or more layers may contain the metal complex of the present invention.

[0092] The organic layer may be a light-emitting layer (emission layer), and the metal complex as described herein may be an emission dopant or a non-emission dopant.

[0093] In a third aspect, the present invention provides a consumer product comprising the above-described organic electroluminescent device.

[0094] The consumer product of the present invention is one or more of the following products: flat panel display, computer monitor, medical monitor, television, signboard, lamp for internal or external lighting and / or signaling, head-up display, fully transparent or partially transparent display, flexible display, laser printer, telephone, cellular phone, tablet computer, phablet, personal digital assistant (PDA), wearable device, laptop computer, digital camera, video camera, viewfinder, microdisplay with a diagonal less than 2 inches, 3-D display, virtual reality or augmented reality display, vehicle, video wall comprising a plurality of tiled displays, theater or stadium screen, light therapy device, and signpost.

[0095] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0096] Using the metal complex of the present invention as a light-emitting material can obtain a green phosphorescent material with high luminous efficiency, and the prepared organic electroluminescent device emits green phosphorescence with high luminous efficiency and good thermal stability. The consumer product of the present invention can obtain electroluminescence with green phosphorescence and high luminous efficiency by containing the organic electroluminescent device of the present invention. Description of the Drawings

[0097] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the following will briefly introduce the drawings required for the description of the embodiments or the prior art. Obviously, the drawings in the following description are only some embodiments of the present invention. For those of ordinary skill in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0098] Figure 1 A schematic diagram of an organic electroluminescent element 100 is shown. The element 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 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111.

[0099] Figure 2 A schematic diagram of an organic electroluminescent element 200 is shown. The element 200 is an example in which a hole blocking layer 107 is added to the element 100.

[0100] Figure 3 A schematic diagram of an organic electroluminescent element 300 with two light-emitting layers is shown. The element 300 includes a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a first light-emitting layer 1061, an electron transport layer 108, a charge generation layer 1022, a hole injection layer 103, a hole transport layer 104, a second light-emitting layer 1063, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer 111. In the element 300, the light-emitting peak shapes of the first light-emitting layer and the second light-emitting layer may be overlapping or cross-overlapping or non-overlapping. Detailed implementation manners

[0101] To make the objectives, technical solutions, and advantages of the present invention clearer, the following will describe the technical solutions of the present invention in detail. Obviously, the described embodiments are only some embodiments of the present invention, rather than all embodiments. Based on the embodiments of the present invention, all other implementation manners obtained by those of ordinary skill in the art without creative efforts fall within the scope of protection of the present invention.

[0102] In the organic electroluminescent element of the present invention, there is no limitation on the constitution of the layer other than the layer containing the metal complex of the present invention. Those skilled in the art can determine the constitution of other layers of the organic electroluminescent element according to the common technical knowledge in the art as needed.

[0103] The "halogen", "halogen atom", "halo group" of the present invention can be used interchangeably and refer to fluorine, chlorine, bromine, or iodine. The "acyl group" of the present invention refers to a substituted carbonyl group (COR). The "ester" of the present invention refers to a substituted oxycarbonyl group (-OCOR or CO 2R). The "ether" of the present invention refers to an -OR group. The "sulfanyl" or "thioether" of the present invention is used interchangeably and refers to an -SR group. The "sulfinyl" of the present invention refers to an -SOR group. The "sulfonyl" of the present invention refers to -SO 2 R group. The "phosphino" of the present invention refers to -PR 3 group, where each R can be the same or different. The "silyl" of the present invention refers to -SiR 3 group, where each R can be the same or different. Each of the above Rs is preferably selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl.

[0104] The "alkyl", "alkenyl", or "alkynyl" of the present invention is preferably considered to refer to the following groups: 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.

[0105] The "alkoxy" of the present invention preferably has an alkoxy group with 1 to 40 carbon atoms and is considered to be methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, and 2,2,2-trifluoroethoxy.

[0106] The "cycloalkyl" and "cycloalkenyl" of the present invention refer to and include monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyls are cycloalkyls containing 3 to 15 ring carbon atoms and can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc., where one or more -CH 2 - groups can be replaced by the above groups; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms, or nitrile groups.

[0107] The "heteroalkyl" or "heterocycloalkyl" of the present invention refers to alkyl or cycloalkyl, preferably alkyl or cycloalkyl having 1 to 40 carbon atoms, and refers to groups in which a single hydrogen atom or -CH 2 - group can be replaced by oxygen, sulfur, halogen atoms, nitrogen, phosphorus, boron, silicon, or selenium, preferably groups replaced by oxygen, sulfur, or nitrogen. Additionally, the heteroalkyl or heterocycloalkyl can be optionally substituted.

[0108] As used herein, the term "heteroalkenyl" or "heterocycloalkenyl" refers to an alkenyl or cycloalkenyl in which at least one carbon atom is replaced by a heteroatom. Optionally, the at least one heteroatom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon or selenium, preferably oxygen, sulfur or nitrogen. Preferred alkenyls and cycloalkenyls are those containing 3 to 15 carbon atoms. Additionally, the heteroalkenyl or heterocycloalkenyl may be optionally substituted.

[0109] As used herein, the terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group substituted by an aryl group. Additionally, the aralkyl may be optionally substituted.

[0110] As used herein, the term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycycle may have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), where at least one of the rings is an aromatic hydrocarbon group, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic and / or heteroaryl. Preferred aryls are those containing 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Particularly preferred are aryls having six, ten or twelve carbon atoms. Suitable aryls include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Additionally, the aryl may be optionally substituted.

[0111] "Heteroaryl" as used in the present invention refers to a monocyclic aromatic group and a polycyclic aromatic ring system that includes at least one heteroatom. Heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, or selenium. In many cases, oxygen, sulfur, or nitrogen are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring can have one to six heteroatoms. The hetero polycyclic system can have two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), where at least one of the rings is a heteroaryl, for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocycle, and / or heteroaryl. The hetero polycyclic aromatic ring system can have one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryls are heteroaryls containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborole, 1,3-azaborole, 1,4-azaborole, borazon, and their nitrogen analogs. Additionally, the heteroaryl can be optionally substituted.

[0112] In the present invention, the term "substituted or unsubstituted" means being substituted with a group selected from hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidino group, hydrazino group, hydrazone group, carboxyl group or its carboxylate, sulfonic acid group or its sulfonate, phosphoric acid group or its phosphate, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C 2 -C 40 alkynyl, C 1 -C 40 alkoxy, C 3 -C 40 cycloalkyl, C 3 -C 40 cycloalkenyl, C 6 -C 60 aryl, C 6 -C 60An aryloxy group, C 6 -C 60 an arylthioether group, and C 2 -C 60 are substituted or unsubstituted by one or more substituents selected from the group consisting of heteroaryl groups, or are substituted or unsubstituted by substituents formed by linking two or more of the above-exemplified substituents.

[0113] In the present invention, "a combination thereof" or "a group" means that one or more members of an applicable list are combined to form a known or chemically stable arrangement that can be envisioned by one of ordinary skill in the art from the applicable list. For example, an alkyl group and deuterium can be combined to form a partially or fully deuterated alkyl group; a halogen and an alkyl group can be combined to form a haloalkyl substituent, such as trifluoromethyl, etc.; and a halogen, an alkyl group, and an aryl group can be combined to form a haloarylalkyl group.

[0114] In one example, the term "substituted" includes combinations of two to four of the listed groups.

[0115] In another example, the term "substituted" includes combinations of two to three groups. In yet another example, the term "substituted" includes combinations of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations including up to forty atoms that are not hydrogen or deuterium, or combinations including up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0116] The names given to the individual layers herein are not intended to be strictly limiting. For example, Figure 3 in, the hole transport layer 104 transports holes and injects holes into the first organic light-emitting layer 1061, and can be described as a hole transport layer, a hole injection layer, an electron blocking layer, or an enhancement layer. In one embodiment, an OLED can be described as having an organic layer disposed between a cathode and an anode. This organic layer can include a single layer or can further include multiple layers of different organic materials as exemplified Figure 1 , Figure 2 or Figure 3 .

[0117] Structures and materials not specifically described can also be used, such as PLEDs containing polymeric materials. As another example, an OLED having a single organic layer or multiple stacks can be used. The OLED structure can deviate from Figure 1 , Figure 2 and Figure 3 the simple layered structure illustrated therein. For example, the substrate can include angled reflective surfaces to improve light coupling.

[0118] Elements fabricated in accordance with embodiments of the present invention may further optionally include a barrier layer. One use of the barrier layer is to protect the electrodes and organic layers from damage due to exposure to harmful substances in the environment, including moisture, vapors, and / or gases, etc. The barrier layer may be deposited on the substrate, on the electrodes, under the substrate, beside the electrodes, or on any other part of the device, including on the edges. 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 compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferably, the barrier layer includes a mixture of a polymeric material and a non-polymeric material. In order to be considered a mixture, the aforementioned polymeric and non-polymeric materials constituting the barrier layer should be deposited under the same conditions and / or simultaneously. 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 consists essentially of polymeric silicon and inorganic silicon.

[0119] In any of the compounds mentioned above used in each layer of the OLED device described above, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically 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.

[0120] The materials and structures described herein may be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use the materials and structures. Further, organic devices such as organic transistors may use the materials and structures.

[0121] These methods are generally known to those of ordinary skill in the art, and they can apply them to organic electroluminescent devices containing compounds according to the present invention without creative effort.

[0122] According to one embodiment, novel ligands of metal complexes are disclosed. The inventors have found that the introduction of these ligands unexpectedly narrows the emission spectrum, reduces the sublimation temperature, and improves the luminous efficiency of the device.

[0123] In embodiments of the present invention, the performance detection conditions of the fabricated electroluminescent device are as follows:

[0124] Luminance and chromaticity coordinates: Measured using a spectral scanner PhotoResearch PR-715;

[0125] Current density and turn-on voltage: Measured using a digital source meter Keithley 2420;

[0126] Power efficiency: Measured using Newport 1931-C.

[0127] Example 1

[0128] Preparation of metal complex Ir(LA128)(LB105) 2 :

[0129] First step: Preparation of compound LA128

[0130]

[0131] Under nitrogen protection, 40.0 mmol of m-phenylphenylboronic acid, 20.0 mmol of diaminomaleonitrile, and 20.0 mmol of p-toluenesulfonic acid were dissolved in 100 mL of toluene, and then 10 g of molecular sieve was added. The temperature was raised to reflux and stirred for 15 hours. After cooling to room temperature, 40.0 mmol of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was added, and the temperature was raised to 80 °C and stirred for 2 hours. After cooling to room temperature, filtration was carried out, and the filtrate was concentrated and dried under reduced pressure, and then separated and purified by silica gel column chromatography to obtain compound LA128, a yellow solid, with a yield of 76%.

[0132] Second step: Preparation of compound Int-1

[0133]

[0134] Under nitrogen protection, 52.9 mmol of compound LB105 and 26.0 mmol of IrCl 3 ·3H 2 O were dispersed in 150 mL of ethylene glycol monoethyl ether and 50 mL of water, and the temperature was raised to reflux and reacted for 24 hours. After cooling to room temperature, filtration was carried out, and the filter cake was washed with water and ethanol and then dried in vacuo to obtain a yellow solid. The obtained yellow solid was dissolved in 250 mL of dichloromethane and 25 mL of methanol, and 30.0 mmol of silver trifluoromethanesulfonate was added, and the mixture was stirred and reacted for 24 hours. After filtration, the filtrate was concentrated and dried under reduced pressure, and the solid was washed with ether to obtain compound Int-1, a brown solid, with a yield of 80%.

[0135] Third step: Preparation of compound Ir(LA128)(LB105) 2 :

[0136]

[0137] Under nitrogen protection, 4.8 mmol of compound LA128 and 2.4 mmol of intermediate Int-1 were dispersed in 50 mL of ethylene glycol monoethyl ether and 50 mL of DMF. The temperature was raised to 120 °C and stirred for reaction for 7 days. After cooling to room temperature, it was concentrated and dried under reduced pressure, and separated and purified by silica gel column chromatography, eluted with dichloromethane - petroleum ether to obtain compound Ir(LA128)(LB105). 2 , brown solid, yield: 58%. MS(ESI): 836.3152[M + . 1 HNMR(δ, CDCl 3 ): 8.79(1H, s); 8.68(2H, s); 7.93 - 7.91(2H, d); 7.86 - 7.84(1H, d); 7.76 - 7.74(3H, m); 7.71 - 7.69(2H, d); 7.52 - 7.47(4H, m); 7.44 - 7.41(2H, m); 7.39 - 7.35(1H, m); 7.23 - 7.21(2H, d).

[0138] Example 2

[0139] Preparation of metal complex Ir(LA170)(LB198) 2 :

[0140] First step: Preparation of compound LA170

[0141]

[0142] Under nitrogen protection, 20.0 mmol of 2 - cyanobenzimidazole was dissolved in 100 mL of dry THF. The temperature was lowered to 0 °C, and 24.0 mmol of 1.0 M methylmagnesium bromide THF solution was added dropwise. Then it was raised to room temperature and stirred for reaction for 1 hour. After cooling to 0 °C, 20 mL of methanol was added dropwise, concentrated and dried under reduced pressure. 20.0 mmol of p - tolylboronic acid, 20.0 mmol of p - toluenesulfonic acid and 100 mL of toluene were added to the residue, and then 10 g of molecular sieve was added. The temperature was raised to reflux and stirred for reaction for 15 hours. After cooling to room temperature, it was filtered, and the filtrate was concentrated and dried under reduced pressure, and separated and purified by silica gel column chromatography to obtain compound LA170, yellow solid, yield 86%.

[0143] Second step: Preparation of compound Int - 2

[0144]

[0145] Referring to the synthesis method of the second step of Example 1, only replacing LB105 in the second step of Example 1 with LB198, compound Int - 2 was obtained, brown solid, yield 84%.

[0146] Step 3: Preparation of the compound Ir(LA170)(LB198) 2 Preparation

[0147]

[0148] Under nitrogen protection, 5.4 mmol of the compound LA170 and 2.4 mmol of the intermediate Int-2 were dispersed in 100 mL of DMF, and the temperature was raised to 120 °C and stirred for reaction for 7 days. After cooling to room temperature, it was concentrated and dried under reduced pressure, and purified by silica gel column chromatography, eluted with dichloromethane-pentane to obtain the compound Ir(LA170)(LB198). 2 , yellow solid, yield: 38%. MS(ESI): 872.3407 [M+H]. 1 HNMR(δ, CDCl 3 ): 8.64(2H, s); 8.06~8.03(4H, m); 7.94~7.92(2H, d); 7.70~7.65(2H, m); 7.61(1H, s); 7.57~7.54(2H, m); 7.46~7.42(2H, m); 7.40~7.37(1H, m); 7.23~7.21(1H, d); 7.17~7.13(2H, m); 7.09~7.04(2H, m); 2.45(3H, s); 2.34(3H, s); 1.18(18H, s).

[0149] Example 3

[0150] Referring to the similar synthesis methods of Example 1 and Example 2, the compound of formula Ir(LAi)(LBj) was prepared 2 shown in the formula, where i is an integer from 1 to 176 and j is an integer from 1 to 432, and the ligands LA1-LA176, LB1-LB432 have the same structures as those described above.

[0151] Example 4

[0152] Preparation of the metal complex Ir(LA1) 2 (LB230), in which the methyl hydrogen atom of LA1 is replaced by deuterium:

[0153] Step 1: Preparation of the compound LA1

[0154]

[0155] Under nitrogen protection, 40.0 mmol of phenylboronic acid, 20.0 mmol of the compound sub-3 and 20.0 mmol of p-toluenesulfonic acid were dissolved in 100 mL of toluene, and then 10 g of Molecular sieve, heated to reflux and stirred for reaction for 15 hours. Cooled to room temperature, 0.1 mol of manganese dioxide and 20 mL of toluene were added, heated to reflux and stirred for reaction for 24 hours. Cooled to room temperature, filtered, the filtrate was concentrated and dried under reduced pressure, and separated and purified by silica gel column to obtain compound LA1, a yellow solid, with a yield of 65%.

[0156] Step 2: Preparation of compound LA1’

[0157]

[0158] Under nitrogen protection, 10.0 mmol of compound LA1 and 10 mL of DMSO-D6 were mixed, and then 20.0 mmol of potassium tert-butoxide was added, heated to 90 °C and stirred for reaction for 24 hours. Cooled to room temperature, the reaction solution was poured into 100 mL of ice water, filtered, the filter cake was washed with water, and separated and purified by silica gel column to obtain compound LA1’, a yellow solid, with a yield of 95%.

[0159] Step 3: Preparation of compound Int-3

[0160]

[0161] Referring to the preparation method in Step 2 of Example 1, only LB105 in Step 2 of Example 1 was replaced with LA1’, and the mass dosage of this compound was changed according to the molar amount, and other experimental parameters were adjusted accordingly according to actual needs to prepare compound Int-3, a brown solid, with a yield of 83%.

[0162] Step 4: Metal complex Ir(LA1) 2 (LB230) preparation

[0163]

[0164] 6.0 mmol of compound LB230 (CAS: 1609374-00-6) and 2.5 mmol of intermediate Int-3 were dispersed in 50 mL of ethylene glycol monoethyl ether and 50 mL of DMF, and under nitrogen protection, heated to 120 °C and stirred for reaction for 7 days. Cooled to room temperature, concentrated and dried under reduced pressure, and separated and purified by silica gel column, eluted with dichloromethane - petroleum ether to obtain compound Ir(LA1) 2 (LB230), a yellow solid, with a yield of 48%. MS(ESI): 806.3326[M+H]. 1 HNMR(δ, CDCl 3):9.22(1H,s); 8.19 - 8.15(1H,m); 8.12 - 8.10(1H,d); 8.09 - 8.06(1H,m); 8.04 - 7.98(4H,m); 7.68 - 7.64(2H,m); 7.29 - 7.27(1H,d); 7.24 - 7.20(3H,m); 6.95 - 6.91(2H,m).

[0165] Example 5

[0166] Metal complex Ir(LA160) 2 (LB364) Preparation:

[0167] First step: Preparation of compound Int-4

[0168]

[0169] Under nitrogen protection, 32.0 mmol of compound LA3 (prepared according to the synthesis methods of the above Examples 1 - 4) and 15.0 mmol of IrCl 3 ·3H 2 O were dispersed in 60 mL of ethylene glycol monoethyl ether and 20 mL of water, and the mixture was heated to reflux for 48 hours. After cooling to room temperature, it was filtered, and the filter cake was washed with water and ethanol and dried under vacuum to obtain a brown solid. The obtained brown solid was dissolved in 100 mL of dichloromethane and 10 mL of methanol, 18.0 mmol of silver trifluoromethanesulfonate was added, and the mixture was stirred for 24 hours. After filtration, the filtrate was concentrated and dried under reduced pressure, and the residue was washed with ether to obtain compound Int-4, a brown solid, with a yield of 68%.

[0170] Second step: Preparation of compound Ir(LA160) 2 (LB364)

[0171]

[0172] 6.0 mmol of compound LB364 and 2.5 mmol of intermediate Int-4 were dispersed in 50 mL of ethylene glycol monoethyl ether and 50 mL of DMF. Under nitrogen protection, the temperature was raised to 120 °C and stirred for 7 days. After cooling to room temperature, it was concentrated to dryness under reduced pressure and purified by silica gel column chromatography, eluted with dichloromethane - petroleum ether, to obtain compound Ir(LA160) 2 (LB364), a brown solid, with a yield of 42%. MS(ESI): 840.0716[M + H]. 1 HNMR(δ, CDCl 3):9.54(1H, s); 8.05 - 7.99(2H, m); 7.87 - 7.84(1H, m); 7.78 - 7.74(2H, m); 7.40 - 7.36(1H, m); 7.15 - 7.11(1H, m).

[0173] Example 6

[0174] Referring to the similar synthesis methods of Example 4 and Example 5, prepare the compound of formula Ir(LAi) 2 (LBj), wherein, i is an integer from 1 to 176, j is an integer from 1 to 432, and LA1 - LA176, LB1 - LB432 have the same meanings as above.

[0175] Example 7

[0176] Preparation of metal complex Ir(LA10) 3 :

[0177] First step: Preparation of compound Int - 5

[0178]

[0179] Disperse 11.0 mmol of compound LA10 (prepared by referring to the synthesis methods of Example 1 - Example 4 above) and 5.0 mmol of IrCl 3 ·3H 2 O in 90 mL of ethylene glycol monoethyl ether and 30 mL of water. Under nitrogen protection, heat to reflux and react for 24 hours. Cool to room temperature, filter, wash the filter cake with water and ethanol, and dry it under vacuum to obtain compound Int - 5, a brown solid, with a yield of 54%.

[0180] Second step: Preparation of compound Ir(LA10) 3 :

[0181]

[0182] Disperse 5.0 mmol of Int - 5 prepared in the first step, 10.0 mmol of silver trifluoromethanesulfonate, and 15.0 mmol of compound LA10 in 20 mL of ethylene glycol monoethyl ether. Under nitrogen protection, heat to reflux and stir for 48 hours. Cool to room temperature, filter, dissolve the filter cake in dichloromethane, and purify it by silica gel column chromatography to obtain compound Ir(LA10) 3 , a brown solid, with a yield of 39%. MS(ESI): 1078.3082[M + . 1 HNMR(δ, CDCl 3):8.92(3H, s); 8.84(3H, s); 8.76(6H, s); 8.62 - 8.60(3H, m); 8.37 - 8.34(3H, m); 7.96 - 7.93(3H, m); 7.88 - 7.80(6H, m); 7.42 - 7.35(6H, m); 7.33 - 7.29(3H, m).

[0183] Example 8

[0184] Referring to the synthesis method of Example 7, appropriately adjust each test parameter and condition to prepare the metal complex Ir(LAi) 3 , where i is an integer from 1 to 176, and LA1 - LA176 have the same meanings as above.

[0185] Preparation of Example 9 Organic Electroluminescent Device

[0186] The preparation method of the OLED device (as shown in Figure 1 ) is as follows:

[0187] Ultrasonically treat the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, rinse it in deionized water, ultrasonically treat it in an acetone / ethanol mixed solvent for 30 minutes, bake it in a clean environment until completely dry, irradiate it with an ultraviolet light cleaning machine for 10 minutes, and bombard the surface with a low-energy cation beam.

[0188] Place the above-treated ITO glass substrate in a vacuum chamber, evacuate to less than 1×10 -5 Pa, evaporate silver as the anode on the above ITO film, and the evaporation film thickness is Continue to evaporate the compound HATCN as the hole injection layer respectively, and the evaporation film thickness is Continue to evaporate the compound HTM as the hole transport layer on the above hole injection layer film, and the evaporation film thickness is

[0189] Evaporate the compound EBM as the electron blocking layer on the aforementioned hole transport layer, and the evaporation film thickness is

[0190] Evaporate the compound H1 and the metal complex of the present invention as the light-emitting layer on the above electron blocking layer. Among them, the metal complex prepared by the present invention is a doping material, and the doping mass is 5% of the compound H1, and the evaporation film thickness is

[0191] Continue to evaporate a layer of LiQ and the compound ETM as the electron transport layer of the device on the above organic light-emitting layer, where LiQ is 50% of the mass of ETM, and the evaporation film thickness is 1

[0192] On the above-mentioned electron transport layer, a layer of LiF is further deposited as the electron injection layer of the device, and the deposited film thickness is

[0193] On the above-mentioned electron injection layer, magnesium and silver are deposited as the cathode of the device. Among them, the mass ratio of magnesium to silver is 1:10, and the deposited film thickness is

[0194] Finally, a compound HTM is deposited on the cathode layer as the capping layer, and the deposited film thickness is Fabricate the organic electroluminescent device of the present invention.

[0195] Comparative Example 1

[0196] Use the compound shown in GD-1 to replace the metal complex of the present invention in Example 9, and the other steps are the same as those in Example 9 to fabricate Comparative Element 1.

[0197] The structural formulas of the aforementioned compounds HATCN, HTM, EBM, H1, LiQ, GD-1, and ETM are shown as follows:

[0198]

[0199] For the above-mentioned fabricated organic electroluminescent device, a digital source meter and a luminance meter are used to measure the driving voltage, current efficiency, and lifespan of the light-emitting device. Specifically, the voltage is increased at a rate of 0.1 V per second, and the voltage when the current density of the organic electroluminescent device reaches 10 mA / cm 2 is measured as the driving voltage, and the luminance at this time is also measured; the ratio of the luminance to the current density is the current efficiency. The LT95% lifespan test is as follows: Using a luminance meter at a luminance of 5000 cd / m 2 while maintaining a constant current, measure the time when the luminance decay of the organic electroluminescent device is 4750 cd / m 2 in hours. The metal complex of the present invention takes Ir(LAi)(LBj) 2 as an example, where i is an integer from 1 to 176, the ligands LA1 to LA176 have the same meaning as above, and the ligand LB is only represented by LB105 as an example. The experimental results are summarized in Table 1, and the * data is normalized compared to Comparative Element 1.

[0200] Table 1

[0201]

[0202]

[0203]

[0204]

[0205]

[0206] As can be seen from Table 1, as a doping material for the light-emitting layer, the metal complex of the present invention has a lower driving voltage compared to Comparative Example 1. In particular, the current efficiency has a significant advantage over Comparative Example 1, and the LT95% life of the device is also very ideal.

[0207] Comparing the compound GD-1 with the metal complex of the present invention, the main difference is that the triplet energy emission of the compound GD-1 is achieved through the metal-to-ligand charge transfer (MLCT) of Ir^N^C, and the phosphorescence lifetime is relatively long, reaching the microsecond level. The ligand LA of the present invention replaces the pyridine in the LUMO unit of GD-1 with a five-membered heterocycle containing a boron atom, and uses the resonance effect of boron-nitrogen to increase the LUMO energy level, thereby increasing the transfer rate of MLCT, reducing the phosphorescence lifetime, and reducing the loss in the energy transfer process. Therefore, the metal complex of the present invention has good stability, improved light-emitting efficiency, and greatly improved light-emitting lifetime, and is a light-emitting material with excellent performance.

[0208] The above is only the specific implementation manner 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, and all of them should be covered by the protection scope of the present invention. Therefore, the protection scope of the present invention should be subject to the protection scope of the claims.

Claims

1. A metal complex, characterized in that The metal complex comprises a ligand LA shown in the following formula: Wherein W is selected from O, S or NR 3 ; X 1 ~X 4 Each independently selected from N or CR 4 ; R 1 ~R 4 is selected, at each occurrence, identically or differently, from hydrogen or from the group consisting of: deuterium, a halogen atom, a nitrile group, an acyl group, a carboxylic acid, an ether, an ester group, an isonitrile group, a sulfide group, a selenoyl group, a sulfinyl group, a sulfonyl group, a phosphine group, a substituted or unsubstituted C1-C 40 Straight chain alkyl, substituted or unsubstituted C1~C 40 Straight chain heteroalkyl, substituted or unsubstituted C3~C 40 Branched or cyclic alkyl, substituted or unsubstituted C3~C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C1~C 40 Straight chain alkoxy, substituted or unsubstituted C3~C 40 Branched or cyclic alkoxy, substituted or unsubstituted C6~C 60 Arylalkyl, substituted or unsubstituted C6~C 60 Aryloxy, substituted or unsubstituted C6~C 60 Aromatic amino, substituted or unsubstituted C3~C 40 Silane, substituted or unsubstituted C2~C 40 Alkenyl, substituted or unsubstituted C4~C 40 Cycloalkenyl, substituted or unsubstituted C2~C 40 Heteroalkenyl, substituted or unsubstituted C2~C 40 Alkynyl, substituted or unsubstituted C6~C 60 Aryl, substituted or unsubstituted C2~C 60 A group consisting of heteroaryl groups, any two or more adjacent R 1 ~R 4 They may be optionally joined or fused to form a substituted or unsubstituted ring, and optionally, the substituent in the case of the substitution is selected from deuterium, a halogen atom, a nitrile group, a hydroxyl group, a C1-C6 straight-chain alkyl group, a C3-C6 branched-chain alkyl group, a C1-C6 straight-chain alkoxy group or a C3-C6 branched-chain alkoxy group; Indicates a single bond or a double bond. When it represents a double bond, R 3 does not exist; The ligand LA is coordinated by the metal M to form a five-membered chelate ring; M is capable of coordinating with other ligands; and the ligand LA is capable of connecting with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand; The M is selected from one of Os, Ir, Pd, Pt, Cu, Ag and Au.

2. The metal complex according to claim 1, characterized in that The chemical formula of the metal complex is M(LA) m (LB) n (LC) r , wherein M, at each occurrence, is identically or differently selected from Pt or Ir; LA, LB and LC are the first ligand, the second ligand and the third ligand coordinated to the metal M, respectively, and LC and LB are the same or different; LA, LB and LC may be optionally linked to form a multidentate ligand; m is 1, 2 or 3, n is 0, 1 or 2, r is 0, 1 or 2, and m+n+r is equal to the oxidation state of the metal M, when m is greater than or equal to 2, the multiple LAs are the same or different; when n is equal to 2, the two LBs are the same or different; when r is equal to 2, the two LCs are the same or different; The LB and LC are selected from any one of the following structures in the same or different manner at each occurrence: Among them, Y 1 ~Y 11 Each independently selected from N or CR 14 , T 1 Selected from BR 12 NR 12 , PR 12 ,O,S,Se,C=O,S=O,SO2,CR 12 R 13 、SiR 12 R 13 and GeR 12 R 13 One of them, R 12 and R 13 They can be arbitrarily joined or fused to form a ring; R 11 , R 12 , R 13 , R 14 are independently selected from hydrogen or the group consisting of deuterium, fluorine, nitrile, substituted or unsubstituted C1-C 40 Straight chain alkyl, substituted or unsubstituted C1~C 40 Straight chain heteroalkyl, substituted or unsubstituted C3~C 40 Branched or cyclic alkyl, substituted or unsubstituted C3~C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C3~C 40 Silane, substituted or unsubstituted C6~C 60 Aryl, substituted or unsubstituted C2~C 60 The group consisting of heteroaryl groups, optionally, the substituents during the above substitution are selected from deuterium, halogen atoms, nitrile groups, hydroxyl groups, C1-C6 straight-chain alkyl groups, C3-C6 branched-chain alkyl groups, C1-C6 straight-chain alkoxy groups or C3-C6 branched-chain alkoxy groups.

3. The metal complex according to claim 1 or 2, characterized in that The chemical formula of the metal complex is Ir(LA) m (LB) n , m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, and m+n=3; When m is 1, the two LBs are the same or different; when m is 2 or 3, the multiple LAs are the same or different; preferably, the chemical formula of the metal complex is Ir(LA)(LB)2, Ir(LA)2(LB) or Ir(LA)3, and the definitions of LA and LB are the same as those in claim 2.

4. The metal complex according to any one of claims 1 to 3, characterized in that LB is selected from the group consisting of LB1-LB432: Alternatively, some or all of the hydrogen atoms in LB may be replaced by deuterium atoms.

5. The metal complex according to claim 1 or 2, characterized in that The metal complex has a structure shown in formula (I): Wherein, m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, and m+n=3; when m is 1, the two LBs are the same or different; when m is 2 or 3, the multiple LAs are the same or different; W, X 1 ~X 4 The same as defined in claim 1; R a ~R h is selected, at each occurrence, identically or differently, from hydrogen or from the group consisting of: deuterium, a halogen atom, a nitrile group, an acyl group, a carboxylic acid, an ether, an ester group, an isonitrile group, a sulfide group, a selenoyl group, a sulfinyl group, a sulfonyl group, a phosphine group, a substituted or unsubstituted C1-C 40 Straight chain alkyl, substituted or unsubstituted C1~C 40 Straight chain heteroalkyl, substituted or unsubstituted C3~C 40 Branched or cyclic alkyl, substituted or unsubstituted C3~C 40 Branched or cyclic heteroalkyl, substituted or unsubstituted C1~C 40 Straight chain alkoxy, substituted or unsubstituted C3~C 40 Branched or cyclic alkoxy, substituted or unsubstituted C6~C 60 Arylalkyl, substituted or unsubstituted C6~C 60 Aryloxy, substituted or unsubstituted C6~C 60 Aromatic amino, substituted or unsubstituted C3~C 40 Silane, substituted or unsubstituted C2~C 40 Alkenyl, substituted or unsubstituted C4~C 40 Cycloalkenyl, substituted or unsubstituted C2~C 40 Heteroalkenyl, substituted or unsubstituted C2~C 40 Alkynyl, substituted or unsubstituted C6~C 60 Aryl, substituted or unsubstituted C2~C 60 The group consisting of heteroaryl groups, any two or more adjacent substituents can be optionally joined or fused to form a substituted or unsubstituted ring; optionally, the substituents in the above substitution are selected from deuterium, halogen atoms, nitrile groups, hydroxyl groups, C1-C6 straight-chain alkyl groups, C3-C6 branched-chain alkyl groups, C1-C6 straight-chain alkoxy groups or C3-C6 branched-chain alkoxy groups.

6. The metal complex according to any one of claims 1 to 5, characterized in that The R 1 ~R 4 , R a ~R h Each independently selected from hydrogen, deuterium, fluorine, nitrile, R A1 ~R A55 , R B1 ~R B45 , R C1 ~R C295 Groups formed; Among them, the R A1 ~R A55 The structural formula is as follows: R B1 ~R B45 The structural formula is as follows: R C1 ~R C295 The structural formula is as follows: Optionally, R A1 -R A55 , R B1 -R B45 and R C1 -R C295 Some or all of the hydrogen atoms in the ion can be replaced by deuterium atoms.

7. The metal complex according to any one of claims 1, 2 or 5, characterized in that The metal complex comprises a ligand LA shown in the following formula: Among them, R 1 and R 2 The same as defined in claim 1, preferably, R 1 and R 2 are the same or different, and are independently selected from hydrogen, deuterium, a nitrile group, a halogen atom, a C1-C6 alkyl group without a substituent, a halogenated C1-C6 alkyl group, a C6-C10 aryl group without a substituent, a C6-C10 aryl group substituted with a C1-C4 alkyl group, a C3-C8 azaaryl group without a substituent, a C3-C8 cycloalkyl group without a substituent, and optionally, R 1 and R 2 The carbon atom connected to it combines to form a C3-C8 cycloalkyl group or a C6-C20 aryl group; Each group of Z1-Z4 is independently selected from CH or N; q is 0, 1, 2 or 3, each R aa independently selected from hydrogen, deuterium, nitrile, halogen, C1-C6 alkyl without substituent, halogenated C1-C6 alkyl, C6-C10 aryl without substituent, C6-C10 aryl substituted by C1-C4 alkyl, C3-C20 nitrogen heteroaryl without substituent, C3-C8 cycloalkyl without substituent, optionally, when q is 2 or 3, the adjacent R aa The carbon atom connected to it combines to form a C3-C8 cycloalkyl group or a C6-C2 aryl group.

8. The metal complex according to any one of claims 1 to 7, characterized in that The LA is selected from the group consisting of LA1-LA176: Alternatively, some or all of the hydrogen atoms in LA1-LA176 may be replaced by deuterium atoms.

9. An organic electroluminescent element comprising a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode, wherein: The organic layer comprises the metal complex according to any one of claims 1 to 8.

10. The organic electroluminescent element according to claim 9, characterized in that: The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron transport layer; The light-emitting layer comprises a main material and a doping material, and the doping material comprises the metal complex according to any one of claims 1 to 8; Preferably, the host material comprises a group consisting of the following compounds: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, nitrogen triphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran and azadibenzoselenophene and derivatives or combinations thereof; Preferably, the mass ratio of the main material to the doping material is 99:1-1:99.

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