Metal complex and application thereof

Abstract

The invention relates to a metal complex and application thereof. The metal complex provided by the invention comprises a structure as shown in a formula (1). According to the metal complex, the organic electroluminescent device with dark blue phosphorescence in electroluminescence and improved luminous efficiency can be obtained, the thermal stability of the luminescent device is good, and the metal complex has wide application prospects in the fields of OLED display and illuminating lamps. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of luminescent materials, and relates to a metal complex and its application. Background Art

[0002] OLED (organic light-emitting diode) utilizes an organic thin film, which emits light when a voltage is applied to the device. OLED is becoming an increasingly concerned technology for applications such as flat panel displays, lighting, and backlighting.

[0003] 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. Currently, red and green phosphorescent materials with a luminous efficiency of 100% are used in OLEDs of various sizes. Although a variety of blue light materials have been widely researched and developed, so far no blue phosphorescent material has been commercialized. There are many dissipation pathways for triplet excitons of phosphorescent materials, such as non-radiative transitions, delayed fluorescence, triplet-triplet annihilation, quenching by oxygen and water vapor, etc., which seriously affect the improvement of phosphorescent performance. It has been found that crystal engineering can utilize strong intermolecular interactions to effectively inhibit non-radiative transitions of triplet excitons, and because of its dense molecular packing, it can reduce the quenching of triplet excitons by oxygen, water vapor, etc., which is an effective way to achieve high-efficiency room-temperature phosphorescence. However, in the crystal aggregate state, intermolecular π-π stacking easily leads to triplet-triplet annihilation, dissipating a large amount of triplet excitons and affecting the improvement of phosphorescent efficiency; and π-π stacking will increase the intermolecular conjugation degree and cause a red shift in luminescence, making it difficult to achieve blue phosphorescence. Therefore, how to construct long-lived and high-efficiency blue phosphorescence remains one of the challenges in the field of organic phosphorescent materials. Summary of the Invention

[0004] In order to solve the above problems existing in the prior art, the present invention provides a metal complex and its application. When the metal complex is used in an OLED, especially in the blue light emission region, it exhibits an enhanced phosphorescence quantum yield and is suitable as an emitter material in OLED applications.

[0005] In a first aspect, the present invention provides a metal complex, which comprises a structure of formula (1):

[0006]

[0007] Wherein, ring A, ring B, ring C, and ring D are each independently selected from a monocyclic or polycyclic fused ring, wherein each ring of the monocyclic and polycyclic fused rings is independently a 5-membered or 6-membered carbon ring or heterocycle, and at least one substituent R is included in ring A, ring B, ring C, and ring D x , the R xThe structure is shown in formula (2):

[0008]

[0009] M represents a metal element with an atomic weight greater than 40;

[0010] X 1 ~X 6 Each is independently selected from C, B or N;

[0011] G is selected from B, N or P;

[0012] Z 1 ~Z 4 Each independently selected from C or N, Z 5 ~Z 19 are independently selected from CH or N; and in Z 5 , Z 6 , Z 7 At least one of them is CH;

[0013] Y 1 , Y 2 , L 1 , L 2 Each independently selected from a single bond, O, S, S=O, SO2, Se, NR 3 , PR 4 , R 4 P=O、CR 4 R 5 、C=O、SiR 4 R 5 ,GeR 4 R 5 or BR 4 ; The condition is that L 1 , L 2 At least one of NR 4 , PR 4 , R 4 P=O、CR 4 R 5 、SiR 4 R 5 ,GeR 4 R 5 or BR 4 , and L 1 , L 2 At least one of the rings connected thereto is fused or joined to form a ring;

[0014] R 1 , R 2 , R 3 , R a , R b , R c and Rd Each represents mono-substituted, di-substituted or poly-substituted to fully saturated substitution, or unsubstituted;

[0015] R a 、R b 、R c 、R d 、R 1 ~R 5 are each independently selected from formula (2), or selected from the group consisting of: hydrogen, deuterium, halogen atom, nitrile group, acyl group, carboxyl group, ether group, ester group, isonitrile group, sulfide group, selenoalkyl group, sulfinyl group, sulfonyl group, phosphino group, substituted or unsubstituted C1-C 40 linear alkyl group, substituted or unsubstituted C1-C 40 linear heteroalkyl group, substituted or unsubstituted C3-C 40 branched or cyclic alkyl group, substituted or unsubstituted C1-C 40 alkoxy group, substituted or unsubstituted C6-C 60 arylalkyl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 arylamino group, substituted or unsubstituted C3-C 40 silyl group, substituted or unsubstituted C2-C 40 alkenyl group, substituted or unsubstituted C4-C 40 cycloalkenyl group, substituted or unsubstituted C2-C 40 heteroalkenyl group, substituted or unsubstituted C2-C 40 alkynyl group, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C2-C 60 heteroaryl group and their combinations. Optionally, any two or more adjacent Rs a 、R b 、R c 、R d 、R 1 ~R 5 can optionally be joined or fused to form a substituted or unsubstituted ring;

[0016] When substituted, the substituents are each independently 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, C1-C 40 alkyl group (such as C1-C6 alkyl group, C7-C 10 alkyl group, C 11 -C 20 alkyl group, etc.), C2-C 40 alkenyl group (such as C2-C6 alkenyl group, C7-C 10 alkenyl group, C 11 -C20 Alkenyl (such as C2-C 40 alkynyl (e.g., C2-C6 alkynyl, C7-C 10 alkynyl, C 11 -C 20 alkynyl, etc.), C1-C 40 alkoxy (e.g., C1-C6 alkoxy, C7-C 10 alkoxy, C 11 -C 20 alkoxy, etc.), C3-C 40 cycloalkyl (e.g., C3-C6 cycloalkyl, C7-C 10 cycloalkyl, C 11 -C 20 cycloalkyl, etc.), C3-C 40 cycloalkenyl (e.g., C3-C6 cycloalkenyl, C7-C 10 cycloalkenyl, C 11 -C 20 cycloalkenyl, etc.), C6-C 60 aryl (e.g., C6-C 12 aryl, C 13 -C 20 aryl, C 21 -C 30 aryl, etc.), C6-C 60 aryloxy (e.g., C6-C 12 aryloxy, C 13 -C 20 aryloxy, C 21 -C 30 aryloxy, etc.), C6-C 60 arylthioether group (e.g., C6-C 12 arylthioether group, C 13 -C 20 arylthioether group, C 21 -C 30 arylthioether group, etc.) and C2-C 60 heteroaryl (e.g., C2-C6 heteroaryl, C7-C 10 heteroaryl, C 11 -C 20 heteroaryl, etc.) in any one or a combination of at least two.

[0017] Indicates the connection position of the substituent R x to rings A, B, C, and D.

[0018] In some embodiments, the ring A is selected from a heteroaromatic ring of C2-C 60 , preferably a heteroaromatic ring of C2-C 20 .

[0019] In some embodiments, the rings B, C and D are selected from aromatic rings having 6 to 60 carbon atoms or heteroaromatic rings having 2 to 60 carbon atoms, preferably aromatic rings having 6 to 20 carbon atoms or heteroaromatic rings having 2 to 20 carbon atoms.

[0020] In some embodiments, the metal complex has a composition of a group of compounds of the formula M(LA)(LB):

[0021]

[0022] wherein, LA-LB is selected from the group consisting of:

[0023]

[0024]

[0025] and / or LA-LB is selected from the group consisting of:

[0026]

[0027]

[0028]

[0029] wherein, W is selected from O, S, CR 6 R 7 , SiR 6 R 7 , CR 6 R 7 -CR 8 R 9 or NR Y ;

[0030] Y is selected from O, S or NR Y ;

[0031] each R Y is the same or different and is independently selected from formula (2) or the group consisting of the following groups: substituted or unsubstituted C1-C 40 linear alkyl, substituted or unsubstituted C3-C 40 branched or cyclic alkyl, substituted or unsubstituted C6-C 60 arylalkyl, substituted or unsubstituted C2-C 40 alkenyl, substituted or unsubstituted C4-C 40 cycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60Heteroaryl and combinations thereof, optionally, R Y may be joined or fused to an adjacent R a , R c or R d to form, optionally, a substituted or unsubstituted ring;

[0032] R 6 to R 9 are each independently selected from hydrogen, or the group consisting of: deuterium, a halogen atom, a nitrile group, an acyl group, a carboxyl group, an ether group, 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 C1-C 40 linear alkyl group, a substituted or unsubstituted C1-C 40 linear heteroalkyl group, a substituted or unsubstituted C3-C 40 branched or cyclic alkyl group, a substituted or unsubstituted C1-C 40 alkoxy group, a substituted or unsubstituted C6-C 60 arylalkyl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylamino group, a substituted or unsubstituted C3-C 40 silyl group, a substituted or unsubstituted C2-C 40 alkenyl group, a substituted or unsubstituted C4-C 40 cycloalkenyl group, a substituted or unsubstituted C2-C 40 heteroalkenyl group, a substituted or unsubstituted C2-C 40 alkynyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C2-C 60 heteroaryl and combinations thereof, optionally, any two or more adjacent R 6 to R 9 may be joined or fused to form, optionally, a substituted or unsubstituted ring;

[0033] When substituted, the substituents are each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazone group, a carboxyl group or its carboxylate salt, a sulfonic acid group or its sulfonate salt, a phosphoric acid group or its phosphate salt, a C1-C 40 alkyl group (e.g., C1-C6 alkyl, C7-C 10 alkyl, C 11 -C 20 alkyl, etc.), a C2-C 40 alkenyl group (e.g., C2-C6 alkenyl, C7-C 10 alkenyl, C 11 -C 20 alkenyl, etc.), a C2-C 40 alkynyl group (e.g., C2-C6 alkynyl, C7-C 10 alkynyl, C11 -C 20 Alkynyl, etc.), C1-C 40 Alkoxy (e.g., C1-C6 alkoxy, C7-C 10 Alkoxy, C 11 -C 20 Alkoxy, etc.), C3-C 40 Cycloalkyl (e.g., C3-C6 cycloalkyl, C7-C 10 Cycloalkyl, C 11 -C 20 Cycloalkyl, etc.), C3-C 40 Cycloalkenyl (e.g., C3-C6 cycloalkenyl, C7-C 10 Cycloalkenyl, C 11 -C 20 Cycloalkenyl, etc.), C6-C 60 Aryl (e.g., C6-C 12 Aryl, C 13 -C 20 Aryl, C 21 -C 30 Aryl, etc.), C6-C 60 Aryloxy (e.g., C6-C 12 Aryloxy, C 13 -C 20 Aryloxy, C 21 -C 30 Aryloxy, etc.), C6-C 60 Arylthio group (e.g., C6-C 12 Arylthio group, C 13 -C 20 Arylthio group, C 21 -C 30 Arylthio group, etc.) and C2-C 60 Heteroaryl (e.g., C2-C6 heteroaryl, C7-C 10 Heteroaryl, C 11 -C 20 Heteroaryl, etc.) or a combination of any one or at least two of them.

[0034] Furthermore, M is selected from Ir, Pt, Pd, Ru, Rh, Os, Au, Cu, Ni, Co, Ga or Ge; preferably, the metal M is selected from Pt or Pd.

[0035] According to an embodiment of the present invention, the metal M is Pt.

[0036] According to an embodiment of the present invention, the metal compound is selected from the group consisting of Pt(LAi)(LBj), where i is an integer from 1 to 24 and j is an integer from 1 to 56, and LA1 to LA24 and LB1 to LB56 have the structures shown above. Some or all of the hydrogen atoms in the structures of LA1 to LA24 and LB1 to LB56 can be replaced by deuterium atoms.

[0037] Further, the L 1 , L 2 are each independently selected from a single bond, O, S, Se, NR 4 , PR 4 , BR 4 , CR 4 R 5 or SiR 4 R 5 .

[0038] Further, the Y 1 , Y 2 are each independently selected from a single bond, O or S.

[0039] Further, the W is selected from O, S, C(CH3)2, C(C6H5)2, Si(CH3)2, Si(C6H5)2 or NR Y .

[0040] Further, the Y is each independently selected from O, S or NR Y .

[0041] Further, the R Y is selected from substituted or unsubstituted C1 - C 40 linear alkyl, substituted or unsubstituted C1 - C 20 linear heteroalkyl, substituted or unsubstituted C3 - C 20 branched or cyclic alkyl, substituted or unsubstituted C1 - C 20 heterocycloalkyl, substituted or unsubstituted C1 - C 20 alkoxy, substituted or unsubstituted C6 - C 30 arylalkyl, substituted or unsubstituted C6 - C 30 aryloxy, substituted or unsubstituted C6 - C 30 arylamino, substituted or unsubstituted C1 - C 20 alkylamino, substituted or unsubstituted C3 - C 20 silyl, substituted or unsubstituted C3 - C 30 arylsilyl, substituted or unsubstituted C2 - C 20 alkenyl, substituted or unsubstituted C4 - C 20 cycloalkenyl, substituted or unsubstituted C2 - C 20Heteroalkenyl, substituted or unsubstituted C2-C 20 Alkynyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 Heteroaryl and combinations thereof;

[0042] When substituted, the substituents are each independently selected from hydrogen, deuterium, halogen atoms, hydroxyl groups, nitrile groups, nitro groups, amino groups, amidino groups, hydrazino groups, hydrazone groups, carboxyl groups or their carboxylates, sulfonic acid groups or their sulfonates, phosphoric acid groups or their phosphates, C1-C 20 Alkyl (such as C1-C6 alkyl, C7-C 10 Alkyl, C 11 -C 20 Alkyl, etc.), C2-C 20 Alkenyl (such as C2-C6 alkenyl, C7-C 10 Alkenyl, C 11 -C 20 Alkenyl, etc.), C2-C 20 Alkynyl (such as C2-C6 alkynyl, C7-C 10 Alkynyl, C 11 -C 20 Alkynyl, etc.), C1-C 20 Alkoxy (such as C1-C6 alkoxy, C7-C 10 Alkoxy, C 11 -C 20 Alkoxy, etc.), C3-C 20 Cycloalkyl (such as C3-C6 cycloalkyl, C7-C 10 Cycloalkyl, C 11 -C 20 Cycloalkyl, etc.), C3-C 20 Cycloalkenyl (such as C3-C6 cycloalkenyl, C7-C 10 Cycloalkenyl, C 11 -C 20 Cycloalkenyl, etc.), C6-C 30 Aryl (such as C6-C 12 Aryl, C 13 -C 20 Aryl, C 21 -C 30 Aryl, etc.), C6-C 30 Aryloxy (such as C6-C 12 Aryloxy, C 13 -C 20 Aryloxy, C 21 -C 30 Aryloxy, etc.), C6-C 30 Arylthio (such as C6-C 12 Arylthio, C 13 -C 20Arylthio group, C 21 -C 30 Arylthio group, etc.) and C2-C 30 Heteroaryl (such as C2-C6 heteroaryl, C7-C 10 Heteroaryl, C 11 -C 20 Heteroaryl, etc.) or a combination of any one or at least two thereof.

[0043] According to an embodiment of the present invention, the R a , R b , R c , R d Each independently selected from formula (2) or the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, an isonitrile group, R A1 ~R A30 , R B1 ~R B195 , R C1 ~R C80 .

[0044] According to an embodiment of the present invention, the Z 5 ~Z 19 Are all CH.

[0045] According to an embodiment of the present invention, the Z 5 Is N; Z 6 ~Z 19 Are all CH.

[0046] According to an embodiment of the present invention, the Z 5 And Z 7 Are N; Z 6 And Z 8 ~Z 19 Are all CH.

[0047] According to an embodiment of the present invention, the Z 6 Is N; Z 5 And Z 7 ~Z 19 Are all CH.

[0048] According to an embodiment of the present invention, the G is selected from B or N.

[0049] According to an embodiment of the present invention, the R x Is selected from the group consisting of formula (3), formula (4), formula (5) or formula (6):

[0050]

[0051] According to an embodiment of the present invention, the R 1 , R 2 , R3 Each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, R A1 ~R A30 、R B1 ~R B195 、R C1 ~R C80 and the group consisting of.

[0052] In some embodiments, two or more adjacent R 1 、R 2 、R 3 may optionally be joined or fused to form a substituted or unsubstituted ring, such as the structures shown in formulas (7) to (11):

[0053]

[0054] wherein Y 3 、Y 4 each independently selected from O, S, Se, NR 10 、PR 10 、BR 10 、CR 10 R 11 or SiR 10 R 11 ;

[0055] G is selected from B or N;

[0056] Said R 10 、R 11 each independently selected from hydrogen, or selected from the group consisting of the following groups: deuterium, substituted or unsubstituted C1-C 40 linear alkyl, substituted or unsubstituted C1-C 40 linear heteroalkyl, substituted or unsubstituted C3-C 40 branched or cyclic alkyl, substituted or unsubstituted C6-C 60 arylalkyl, 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 heteroaryl and combinations thereof, any two or more adjacent R 10 and R 11 may optionally be joined or fused to form a substituted or unsubstituted ring;

[0057] , optionally, the ring is substituted with one or more substituents selected from hydrogen, deuterium, halogen atoms, hydroxyl groups, nitrile groups, nitro groups, amino groups, C1-C6 alkyl groups, C1-C6 alkoxy groups, C3-C10 cycloalkyl groups, C6-C10 aryl groups, and C2-C10 heteroaryl groups.

[0058] Further, the Y 3 , Y 4 are each independently selected from O, S, C(CH3)2, C(C6H5)2, Si(CH3)2, Si(C6H5)2, or NR 10 .

[0059] According to an embodiment of the present invention, the Y 3 , Y 4 are each independently selected from O, S, or C(CH3)2.

[0060] According to an embodiment of the present invention, the Y 3 , Y 4 are each independently selected from O or S.

[0061] According to an embodiment of the present invention, the R 4 ~R 9 are each independently selected from the group consisting of a hydrogen atom, R A1 ~R A25 , R B1 ~R B185 , R C1 ~R C79 .

[0062] According to an embodiment of the present invention, the R Y is each independently selected from formula (2) or from the group consisting of R A1 ~R A25 , R B1 ~R B185 , R C1 ~R C79 .

[0063] The structural formulas of the R A1 ~R A30 are shown as follows:

[0064]

[0065]

[0066] The structures of the R B1 ~R B195 are shown as follows:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072] The said R C1 ~R C80 The structure shown is as follows:

[0073]

[0074]

[0075] Each hydrogen atom in each substituent can be replaced by a deuterium atom.

[0076] In some embodiments, the metal complex is selected from the structures shown by the following formula, wherein at least one substituent R x is substituted, preferably substituted by 1 or 2 substituents R x :

[0077]

[0078]

[0079]

[0080] Wherein, R x , R a , R b , R c , R d has the definition described in the present invention.

[0081] In some embodiments, R a , R b , R c , R d are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, an isonitrile group, R A1 ~R A30 , R B1 ~R B195 , R C1 ~R C80 .

[0082] In some embodiments, R a , R b , R c , R dEach is independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, an isonitrile group, an unsubstituted C1-C6 alkyl group, a deuterium-substituted C1-C6 alkyl group, a C1-C4 alkyl-substituted C6-C10 aryl group, and a C1-C4 alkyl-substituted C4-C15 heteroaryl group, preferably selected from a hydrogen atom, a deuterium atom, fluorine, a nitrile group, an isonitrile group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a deuterated methyl group (e.g., -CD3), a deuterated ethyl group or the following groups:

[0083]

[0084] In some embodiments, R x is selected from the group consisting of formula (3), formula (4), formula (5) or formula (6):

[0085]

[0086] R 1 , R 2 , R 3 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, R A1 to R A30 , R B1 to R B195 , R C1 to R C80 , optionally any two or more adjacent R 1 -R 5 can be optionally joined or fused to form a substituted or unsubstituted ring.

[0087] In some embodiments, R x is selected from the group consisting of the following groups:

[0088]

[0089]

[0090] wherein G is selected from B or N, and each of R 1A and R 2A is independently selected from a hydrogen atom, a deuterium atom, fluorine, a nitrile group, an isonitrile group, an unsubstituted C1-C6 alkyl group, a deuterium-substituted C1-C6 alkyl group, preferably selected from a hydrogen atom, a deuterium atom, fluorine, a nitrile group, an isonitrile group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group or a tert-butyl group.

[0091] In the substituted or unsubstituted ring formed by the binding of adjacent groups to each other in the present invention, the "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The term "bonding" to form a ring refers to a fused ring, and a fused ring refers to a fused aliphatic ring, a fused aromatic ring, a fused aliphatic heterocyclic ring, a fused aromatic heterocyclic ring, or a form formed by their combination. The term "fused" ring refers to two aromatic rings joined together by a shared single bond or double bond. As non-limiting examples, for instance, two benzene rings are fused to form a naphthalene ring, a benzene ring and a furan ring are fused to form benzofuran, two benzene rings and a furan ring are fused to form dibenzofuran, etc.

[0092] The "aryl" or "aromatic ring" according to the present invention refers to and includes a monocyclic aromatic hydrocarbon group and a polycyclic aromatic ring system. The polycycle can 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. For example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl or aromatic rings are aryl groups containing 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Particularly preferred are aryl groups having six, ten, or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthryl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, indenyl, and azulyl, preferably phenyl, biphenyl, terphenyl, triphenylene, fluoranthenyl, and naphthyl. Additionally, the aryl group can be optionally substituted.

[0093] "Heteroaryl" or "heteroaromatic ring" in the sense of the present invention refers to a monocyclic aromatic group and a polycyclic aromatic ring system containing 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 is a preferred heteroatom. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring may have one to six heteroatoms. The hetero polycyclic system may 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 heteroaryl, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocycle, and / or heteroaryl. The hetero polycyclic aromatic ring system may have one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryl is heteroaryl containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl includes dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, furyl, thienyl, benzofuranyl, benzothienyl, benzoselenophenyl, carbazolyl, indolocarbazolyl, pyridylindolyl, pyrrolodipyridyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, oxatriazolyl, dioxazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazinyl, oxathiazinyl, oxadiazinyl, indolyl, benzimidazolyl, indazolyl, indoxazinyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phthalazinyl, pteridinyl, xanthenyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, benzofuranopyridyl, furanodipyridyl, benzothiophenopyridyl, thiophenodipyridyl, benzoselenophenopyridyl, selenophenodipyridyl, 1,2-azaborolyl, 1,3-azaborolyl, 1,4-azaborolyl, borazynyl and its nitrogen analogs, preferably dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl, indolocarbazolyl, imidazolyl, pyridyl, triazinyl, benzimidazolyl, 1,2-azaborolyl, 1,3-azaborolyl, 1,4-azaborolyl, borazynyl and its nitrogen analogs. Additionally, the heteroaryl may be optionally substituted.

[0094] The aryl or heteroaryl according to the present invention particularly refers to a group derived from the following substances: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, Groups including a base, a perylene group, a fluoranthene group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, a diphenyl group, a terphenyl group, a triphenyl group, a quaterphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthryl group, a triphenylene group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis- or trans-indeno[1,2-b]fluorene group, a cis- or trans-indeno[1,2-b]carbazole group, a cis- or trans-indolo[1,2-b]carbazole group, a trindene group, an isotrindene group, a spirotrindene group, a spiroisotrindene group, a furyl group, a benzofuryl group, an isobenzofuryl group, a dibenzofuryl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, an acridinyl group, a phenanthridinyl group, a benzo[5,6]quinolinyl group, a benzo[6,7]quinolinyl group, a benzo[7,8]quinolinyl group, a phenothiazinyl group, a phenoxazinyl group, a pyrazolyl group, a benzopyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthimidazolyl group, a phenanthrimidazolyl group, a pyridinimidazolyl group, a pyrazinimidazolyl group, a quinoxalinimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, an anthroxazolyl group, a phenanthroxazolyl group, an isoxazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a hexaazatriphenylene group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1,5-diazaanthracenyl group, a 2,7-diazapyrenyl group, a 2,3-diazapyrenyl group, a 1,6-diazapyrenyl group, a 1,8-diazapyrenyl group, a 4,5-diazapyrenyl group, a 4,5,9,10-tetraazaperylene group, a pyrazinyl group, a phenazinyl group, a phenoxazinyl group, a phenothiazinyl group, a fluoranthene ring group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbazolyl group, a carbazolyl group, a phenanthrolinyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a benzotriazolyl group, a 1,2,3-oxadiazolyl group, a 1,2,4-oxadiazolyl group, a 1,2,5-oxadiazolyl group, a 1,3,4-oxadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,5-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,3,5-triazinyl group, a 1,2,4-triazinyl group, a 1,2,3-triazinyl group, a tetrazolyl group, a 1,2,4,5-tetrazinyl group, a 1,2,3,4-tetrazinyl group, a 1,2,3,5-tetrazinyl group, a purinyl group, a pteridinyl group, an indazyl group, a quinazolinyl group, a benzothiadiazolyl group, a 1,3,2-diazaborolyl group, a 1,3,2-benzo-diazaborolyl group, or a group derived from a combination of these systems.

[0095] "Alkyl" in the sense of the present invention includes straight-chain and branched-chain alkyl groups. The alkyl group can be an alkyl group having 1 to 40 carbon atoms, preferably an alkyl group having 1 to 20 carbon atoms, and more preferably an alkyl group having 1 to 12 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. Additionally, the alkyl group can be optionally substituted.

[0096] "Cycloalkyl" refers to a cyclic alkyl group, including monocyclic, polycyclic and spiroalkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 40 ring carbon atoms, preferably a cycloalkyl group having 4 to 20 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. Additionally, the cycloalkyl group can be optionally substituted.

[0097] "Heterocycloalkyl" in the sense of the present invention refers to a cycloalkyl group in which a single hydrogen atom or -CH2- group can be substituted by an oxygen, sulfur, halogen atom, nitrogen, phosphorus, boron, silicon or selenium atom, preferably a group substituted by oxygen, sulfur or nitrogen. Additionally, the heteroalkyl or heterocycloalkyl group can be optionally substituted.

[0098] "Alkenyl" encompasses straight-chain, branched-chain and cyclic olefin groups. The alkenyl group can be an alkenyl group containing 2 to 40 carbon atoms, preferably an alkenyl group having 2 to 20 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. Additionally, the alkenyl group can be optionally substituted.

[0099] "Alkynyl" encompasses straight-chain alkynyl groups. The alkynyl group can be an alkynyl group containing 2 to 40 carbon atoms, preferably an alkynyl group having 2 to 20 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenyl ethynyl, phenyl propynyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenyl ethynyl are preferred. Additionally, the alkynyl group can be optionally substituted.

[0100] "Cycloalkenyl" refers to a cyclic olefin group, including monocyclic, polycyclic, and spiro cycloalkenyl groups. Preferred cycloalkenyl groups are those containing 3 to 15 ring carbon atoms, such as cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc.; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms, or nitrile groups.

[0101] "Heteroalkenyl" or "heterocycloalkenyl" in the sense of the present invention refers to an alkenyl or cycloalkenyl group 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 alkenyl and cycloalkenyl groups are those containing 3 to 15 carbon atoms. Additionally, heteroalkenyl and heterocycloalkenyl groups can be optionally substituted.

[0102] "Heteroalkyl" is formed by replacing one or more carbons in an alkyl chain with a heteroatom selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, phosphorus atoms, silicon atoms, germanium atoms, and boron atoms. The heteroalkyl can be a heteroalkyl having 1 to 40 carbon atoms, preferably a heteroalkyl having 1 to 20 carbon atoms, more preferably a heteroalkyl having 1 to 12 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.

[0103] "Alkoxy" in the sense of the present invention is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heteroalkenyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heteroalkenyl are the same as those described above. The alkoxy may be an alkoxy having 1 to 40 carbon atoms, preferably an alkoxy having 1 to 20 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy may be optionally substituted.

[0104] "Selenoalkyl" is represented by -Se-alkyl, -Se-cycloalkyl, -Se-heteroalkyl or -Se-heteroalkenyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heteroalkenyl are the same as those described above. The selenoalkyl may be a selenoalkyl having 1 to 40 carbon atoms, preferably a selenoalkyl having 1 to 20 carbon atoms. Examples of selenoalkyl include methylseleno, ethylseleno, propylseleno, butylseleno, pentylseleno, hexylseleno, cyclopropylseleno, cyclobutylseleno, cyclopentylseleno, cyclohexylseleno, tetrahydrofurylseleno, tetrahydropyranylseleno, methoxypropylseleno, ethoxyethylseleno, methoxymethylseleno and ethoxymethylseleno, etc. Additionally, the selenoalkyl may be optionally substituted.

[0105] "Acyl" in the sense of the present invention refers to a substituted carbonyl (COR a ).

[0106] "Carboxyl" or "carboxylic acid group" in the sense of the present invention refers to a substituted carboxyl (R a COOH).

[0107] "Ester group" in the sense of the present invention refers to a substituted oxycarbonyl (-OCOR a or CO2R a ).

[0108] "Ether group" in the sense of the present invention refers to -OR a group.

[0109] "Thio group" or "thioether" as described herein are used interchangeably and refer to -SR a group.

[0110] "Sulfinyl group" in the sense of the present invention refers to -SOR a group.

[0111] "Sulfonyl group" in the sense of the present invention refers to -SO2R a group.

[0112] "Phosphino group" in the sense of the present invention refers to -PR a3 groups, where each R a may be the same or different.

[0113] Each of the above R a , preferably selected from the group consisting of alkyl, cycloalkyl, aryl, and heteroaryl.

[0114] Aryloxy is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those above. Aryloxy may be an aryloxy having 6 to 60 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, aryloxy may be optionally substituted.

[0115] The arylphosphino group used in the present invention refers to a diarylphosphino group substituted by an aryl having 6 to 60 carbon atoms. As non-limiting examples of the arylphosphino group, there are diphenylphosphino group, bis(4-trimethylsilylbenzene)phosphino group, etc. The aryloxyphosphino group is the phosphorus atom of the diarylphosphino group oxidized to the highest valence state.

[0116] The arylamino group or arylamine group used in the present invention refers to an amino group substituted by an aryl having 6 to 60 carbon atoms. As non-limiting examples of the arylamino group, there are diphenylamino group, carbazolyl group, etc.

[0117] "Halogen", "halogen atom", "halo group" in the sense of the present invention are used interchangeably and refer to fluorine, chlorine, bromine, or iodine.

[0118] Arylalkyl or aryl-alkyl can be used interchangeably and encompasses an alkyl substituted by an aryl. Arylalkyl may be an arylalkyl having 7 to 60 carbon atoms, preferably an arylalkyl having 7 to 40 carbon atoms, more preferably an arylalkyl having 7 to 20 carbon atoms. Examples of arylalkyl include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, arylalkyl may be optionally substituted.

[0119] Alkylsilyl or silyl encompasses alkyl-substituted silyl. It can be an alkylsilyl having 3 to 40 carbon atoms, preferably an alkylsilyl having 3 to 20 carbon atoms. Examples of alkylsilyl include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, methyl-di-tert-butylsilyl. Additionally, the alkylsilyl can be optionally substituted.

[0120] Arylsilyl encompasses silyl substituted with at least one aryl. The arylsilyl can be an arylsilyl having 6 to 60 carbon atoms, preferably an arylsilyl having 8 to 40 carbon atoms. Examples of arylsilyl include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyl-tert-butylsilyl. Additionally, the arylsilyl can be optionally substituted.

[0121] Alkylgermyl encompasses alkyl-substituted germyl. The alkylgermyl can be an alkylgermyl having 3 to 40 carbon atoms, preferably an alkylgermyl having 3 to 20 carbon atoms. Examples of alkylgermyl include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tri-tert-butylgermyl, triisobutylgermyl, dimethyl-tert-butylgermyl, methyl-di-tert-butylgermyl. Additionally, the alkylgermyl can be optionally substituted.

[0122] Arylgermyl encompasses germyl substituted with at least one aryl or heteroaryl. The arylgermyl can be an arylgermyl having 6 to 60 carbon atoms, preferably an arylgermyl having 8 to 40 carbon atoms. Examples of arylgermyl include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyl-tert-butylgermyl. Additionally, the arylgermyl can be optionally substituted.

[0123] In the present disclosure, the term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or at least two C-H groups in the corresponding aromatic moiety are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those of ordinary skill in the art can readily envision other nitrogen analogs of the above-described aza derivatives, and all such analogs are determined to be included in the terms described herein.

[0124] In many cases, the general substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxyl, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, and phosphino.

[0125] As used herein, the term "substituted or unsubstituted" means being substituted or unsubstituted by one or more substituents selected from hydrogen, deuterium, halogen atom, hydroxyl, nitrile, nitro, amino, amidino, hydrazino, hydrazono, carboxyl or its carboxylate, sulfonic acid group or its sulfonate, phosphoric acid group or its phosphate, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C1-C 40 alkoxy, C3-C 40 cycloalkyl, C3-C 40 cycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthioether group and C2-C 60 heteroaryl, or being substituted or unsubstituted by a substituent formed by linking two or more of the above-exemplified substituents.

[0126] As used herein, "a combination thereof" or "a group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that a person of ordinary skill in the art can envision from the applicable list. For example, an alkyl and deuterium can be combined to form a partially or fully deuterated alkyl; a halogen and an alkyl can be combined to form a haloalkyl substituent, such as difluoromethyl, trifluoromethyl, etc.; and a halogen, an alkyl, and an aryl can be combined to form a haloaralkyl.

[0127] In one example, the term "substituted" includes a combination of two to four of the listed groups.

[0128] In another instance, the term "substituted" includes combinations of two to three groups. In yet another instance, 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, the preferred combination of substituents will include up to twenty atoms that are not hydrogen or deuterium in combination.

[0129] In the compounds mentioned in the present disclosure, unless explicitly defined, such as adjacent substituents can optionally be linked to form a ring, adjacent substituents in the compounds cannot be linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally be linked to form a ring, which includes both the case where adjacent substituents can be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be linked to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spiro rings, bridged rings, fused rings, etc.), as well as an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0130] According to an embodiment of the present invention, the metal complex is selected from the group consisting of:

[0131]

[0132]

[0133]

[0134]

[0135] wherein G is selected from B or N;

[0136] Some or all of the hydrogen atoms in the above structure can be replaced by deuterium atoms.

[0137] In a second aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, and at least one of the organic layers contains the metal complex of formula (1) described above.

[0138] The organic electroluminescent device of the present invention may further include a light-emitting layer, and the light-emitting layer contains the metal complex as disclosed above in the present disclosure.

[0139] According to an embodiment of the present invention, the light-emitting layer in the organic electroluminescent device emits blue light.

[0140] According to an embodiment of the present invention, the light-emitting layer comprises an organic electroluminescent material, and the organic electroluminescent material comprises a metal complex represented by formula (1) disclosed herein.

[0141] In some embodiments, the organic electroluminescent material may further comprise other compounds, such as fluorescent emitters, delayed fluorescent emitters, and combinations thereof.

[0142] Furthermore, the light-emitting layer further includes a host material and a dopant material, and the dopant material includes the metal complex of the present invention; the host material may include one or more; when the host material is a combination of multiple types, it includes at least one n-type host compound and at least one p-type host compound.

[0143] According to an embodiment of the present invention, the light-emitting layer in the organic electroluminescent device contains the organic electroluminescent material of the present invention. Further, the organic electroluminescent material contains the metal complex disclosed in the present invention.

[0144] According to an embodiment of the present invention, at least one of the host materials is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phenanthryl, azaphenanthryl, pyrimidinyl, triazine, triphenylene, carbazolyl, indolocarbazolyl, dibenzothiophenyl, dibenzofuranyl, fluorenyl, silafuorenyl, dibenzoselenophenyl, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracenyl, aza-triphenylene, aza-carbazolyl, aza-indolocarbazolyl, aza-dibenzothiophenyl, aza-dibenzofuranyl, aza-dibenzoselenophenyl, and aza-(5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene) group or a combination derived from these systems.

[0145] The organic layer of the present invention may be a light-emitting layer and the metal complex as described herein may be an emissive dopant compound or a non-emissive dopant compound.

[0146] Furthermore, the dopant material is 0.1% to 100% of the mass of the light-emitting layer, such as 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 60%, 70%, 80%, 90% or any value therebetween.

[0147] Preferably, the dopant material is 1% to 50% of the mass of the light-emitting layer.

[0148] Even further, the dopant material is 1% to 30% of the mass of the light-emitting layer.

[0149] Preferably, the main material is selected from the group consisting of the following structures:

[0150]

[0151] According to an embodiment of the present invention, the organic electro-optic device further includes a hole injection layer, which can be a single-material functional layer or a functional layer containing multiple materials. Among them, the most common multiple materials are hole transport materials doped with a certain proportion of p-type conductive doping materials. Common p-type doping materials include:

[0152]

[0153] According to another embodiment of the present invention, a composition is also disclosed, which contains a metal complex, and the specific structure of the metal complex is as shown in any of the foregoing embodiments.

[0154] The materials described herein as suitable for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the emissive dopant compounds disclosed herein can be combined with a wide variety of hosts, transport layers, blocking 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.

[0155] These methods are generally known to those of ordinary skill in the art, and they can apply them to organic electroluminescent elements containing the compounds according to the present invention without creative efforts.

[0156] In a third aspect, the present invention provides a consumer product including the organic electroluminescent device described above.

[0157] The consumer product of the present invention can be one of the following products: flat panel display, computer monitor, medical monitor, television, billboard, 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 including multiple tiled displays, theater or stadium screen, light therapy device, and sign.

[0158] Compared with the prior art, the beneficial effects of the present invention are:

[0159] (1) When the metal complex of the present invention is used in OLED, especially in the blue light emission region, it exhibits enhanced phosphorescence quantum yield, good luminescence stability, high luminescence efficiency, and is suitable for use as an emission dopant (dopant material) in OLED applications. The metal complex 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 organic light-emitting device 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;

[0160] (2) The metal complex 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.

[0161] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to nuclear magnetic resonance, liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, fluorescence spectrophotometer, electrochemical workstation, sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to evaporation machine, optical test system, life test system, ellipsometer, etc.). Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned relevant contents will not be elaborated in this patent. BRIEF DESCRIPTION OF THE DRAWINGS

[0162] 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.

[0163] Figure 1Schematic diagram showing an organic electroluminescent device 100. 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, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the described layers.

[0164] Figure 2 Schematic diagram showing an organic electroluminescent device 200 having 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 emission peak shapes of the first light emitting layer and the second light emitting layer may be overlapping or cross-overlapping or non-overlapping. Detailed Description

[0165] To make the objectives, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention will be described in detail below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without any creative efforts fall within the scope of protection of the present invention.

[0166] "EQE" in the present invention refers to the external quantum efficiency of an element, that is, the ratio of the number of photons emitted by the element to the number of electrons injected into the element.

[0167] 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 may be used in conjunction with a wide variety of other structures. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, the hole transport layer 204 transports holes and injects holes into the light emitting layer 205, and may be described as a hole transport layer or an electron blocking layer. In one embodiment, an 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 multiple layers of different organic materials as described in, for example, Figure 1 and Figure 2 described.

[0168] Structures and materials not specifically described may also be used, such as PLEDs containing polymeric materials. As another example, an OLED having a single organic layer or multiple stacks may be used. The OLED structure may deviate from Figure 1 and Figure 2The simple hierarchical structure described in [reference]. For example, the substrate may include angled reflective surfaces to improve light coupling.

[0169] 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, ethyl, isopropyl, tert-butyl, 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.

[0170] The materials and structures described herein can be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can use the materials and structures.

[0171] Furthermore, organic devices such as organic transistors can use the materials and structures.

[0172] In the following embodiments of the present invention, unless otherwise specified, conventional preparation methods are used. The raw materials used can be obtained from public commercial sources unless otherwise specified, and the percentages are mass percentages unless otherwise specified.

[0173] To more clearly illustrate the present invention, the technical solutions of the present invention are described below in conjunction with some specific embodiments:

[0174] In the embodiments of the present invention, the performance detection conditions of the prepared electroluminescent device are as follows:

[0175] Chromaticity coordinates: measured using a spectral scanner PhotoResearch PR-715;

[0176] Current-voltage: measured using a digital source meter Keithley 2420;

[0177] Power efficiency: measured using a NEWPORT 1931-C;

[0178] Luminance: measured using a luminance meter Minolta Cs-1000A.

[0179] Example 1

[0180] The preparation of Compounds A1 - A11 includes the following steps:

[0181] First step: The preparation of Compound Int-1

[0182]

[0183] Under nitrogen protection, 10.0 mmol of 2-bromo-5-chloro-1,3-diiodobenzene, 22.0 mmol of 1-naphthaleneboronic acid, 50.0 mmol of anhydrous sodium carbonate and 0.01 mmol of Pd(PPh3)4 were mixed, and then 20 mL of toluene, 10 mL of ethanol and 10 mL of water were added. The temperature was raised to 40 °C and stirred for reaction for 24 hours. 50 mL of water was added to the reaction solution, and it was extracted with ethyl acetate. The organic phase was dried, filtered, and the filtrate was concentrated to dryness under reduced pressure and separated and purified by silica gel column chromatography to obtain compound Int-1, a white solid, with a yield of 62%.

[0184] Step 2: Preparation of compound A1

[0185]

[0186] Under nitrogen protection, 10.0 mmol of compound Int-1 was dissolved in 80 mL of m-xylene, the temperature was lowered to -30 °C, and 13.0 mmol of 2.5 M n-butyllithium hexane solution was added dropwise. The temperature was raised to room temperature and stirred for reaction for 2 hours. The temperature was lowered to -30 °C, and then 13.5 mmol of boron tribromide was added dropwise and stirred for reaction for 30 minutes. The temperature was raised to 50 °C and stirred for reaction for 3 hours. The temperature was lowered to 0 °C, and 25.6 mmol of diisopropylethylamine was added dropwise. The temperature was raised to room temperature and stirred for reaction for 2 hours. The temperature was raised to reflux and the low-boiling solvent was distilled off to make the temperature reach above 140 °C, and stirred for reaction for 15 hours. It was cooled to room temperature, concentrated to dryness under reduced pressure, and separated and purified by silica gel column chromatography to obtain compound A1, an orange solid, with a yield of 36%.

[0187]

[0188] Preparation of compound A2: Referring to the above synthesis method of A1, only 1-naphthaleneboronic acid in the first step was replaced by 4-tert-butyl-1-naphthaleneboronic acid to obtain compound A2, an orange solid, with a yield of 32%.

[0189]

[0190] Preparation of compound A3: Referring to the above synthesis method of A1, only 1-naphthaleneboronic acid in the first step was replaced by 1,1,2,2-tetramethyl-5-acenaphtheneboronic acid to obtain compound A3, an orange solid, with a yield of 35%.

[0191]

[0192] Preparation of compound A4: Referring to the above synthesis method of A1, only 1-naphthaleneboronic acid in the first step was replaced by 1-phenanthreneboronic acid to obtain compound A4, an orange solid, with a yield of 38%.

[0193]

[0194] Preparation of Compound A5: Referring to the synthesis method of A1 above, only replace 1-naphthaleneboronic acid in the first step with 4-tert-butyl-1-phenanthreneboronic acid to obtain Compound A5, an orange solid, with a yield of 32%.

[0195]

[0196] Preparation of Compound A6: Referring to the synthesis method of A1 above, only replace 1-naphthaleneboronic acid in the first step with 1-benzo[4,5-bcd]furanylboronic acid to obtain Compound A6, a yellow solid, with a yield of 28%.

[0197]

[0198] Preparation of Compound A7: Under nitrogen protection, 10.0 mmol of Compound A2’ (prepared according to the synthesis method of A2 above) was dissolved in 90 mL of dichloromethane and 30 mL of glacial acetic acid. 10.0 mmol of N-bromosuccinimide (NBS) was added, and the mixture was stirred at room temperature for 12 hours. 100 mL of water was added to the reaction solution, and the organic phase was separated. The aqueous phase was extracted with dichloromethane. The organic phase was dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. It was separated and purified by silica gel column chromatography and recrystallized from dichloromethane / methanol to obtain Compound A7, an orange solid, with a yield of 90%.

[0199]

[0200] Preparation of Compound A8: Referring to the synthesis method of Compound A7 above, only replace Compound A2’ with Compound A3’ (prepared according to the synthesis method of A3 above) to obtain Compound A8, an orange solid, with a yield of 92%.

[0201]

[0202] Preparation of Compound A9: Referring to the synthesis method of Compound A1 above, replace 1-naphthaleneboronic acid in the first step with 1-phenanthrenylboronic acid, and replace 2-bromo-5-chloro-1,3-diiodobenzene with 2-bromo-4-chloro-1,3-diiodobenzene to obtain Compound A9, an orange solid, with a yield of 33%.

[0203]

[0204] Preparation of Compound A10: Referring to the synthesis method of Compound A1 above, replace 1-naphthaleneboronic acid in the first step with 4-tert-butyl-1-phenanthrenylboronic acid, and replace 2-bromo-5-chloro-1,3-diiodobenzene with 2-bromo-4-chloro-1,3-diiodobenzene to obtain Compound A10, an orange solid, with a yield of 35%.

[0205]

[0206] Preparation of Compound A11: Referring to the synthesis method of Compound A1 above, replace 1-naphthaleneboronic acid in the first step with 1-benzo[4,5-bcd]furanylboronic acid, and replace 2-bromo-5-chloro-1,3-diiodobenzene with 2-bromo-4-chloro-1,3-diiodobenzene to obtain Compound A11, an orange solid with a yield of 31%.

[0207]

[0208] Preparation of Compound A12: Referring to the synthesis method of Compound A1 above, only replace 1-naphthaleneboronic acid in the first step with 1-anthracenylboronic acid to obtain Compound A12, an orange solid with a yield of 38%.

[0209]

[0210] Preparation of Compound A13: Referring to the synthesis method of Compound A1 above, replace 1-naphthaleneboronic acid in the first step with 1-anthracenylboronic acid, and replace 2-bromo-5-chloro-1,3-diiodobenzene with 2-bromo-4-chloro-1,3-diiodobenzene to obtain Compound A13, an orange solid with a yield of 35%.

[0211] Example 2

[0212] Preparation of Metal Complex P20 (G = B) includes the following steps:

[0213] First Step: Preparation of Compound Int-2

[0214]

[0215] Under nitrogen protection, mix 10.0 mmol of Compound A7, 15.0 mmol of o-nitroaniline, 15.0 mmol of sodium tert-butoxide, 0.1 mmol of Pd2(dba)3CHCl3 and 80 mL of toluene, then add 0.2 mmol of Xanthphos, heat to 100 °C, and stir the reaction for 15 hours. Cool to room temperature, add 40 mL of water, separate the organic phase, extract the aqueous phase with ethyl acetate, combine and dry the organic phases, filter, concentrate the filtrate under reduced pressure to dryness, and purify by silica gel column chromatography to obtain Compound Int-2, a yellow solid with a yield of 84%.

[0216] Second Step: Preparation of Compound Int-3

[0217]

[0218] Mix 20.0 mmol of the compound Int-2 prepared in the previous step with 1.0 g of 10% palladium on carbon, then add 80 mL of ethanol, and displace with hydrogen three times. Pass hydrogen at room temperature, stir the reaction at atmospheric pressure for 10 hours, filter, concentrate the filtrate under reduced pressure to dryness to obtain the compound Int-3, a yellow solid, which is directly used in the next step without purification, with a yield of 100%.

[0219] Step 3: Preparation of compound Int-4

[0220]

[0221] Under nitrogen protection, mix 10.0 mmol of the compound PC-1 (CAS: 2929353-68-2), 11.0 mmol of the compound Int-3, 15.0 mmol of sodium tert-butoxide, 0.1 mmol of Pd2(dba)3 and 80 mL of toluene, then add 0.2 mmol of 10% tri-tert-butylphosphine toluene solution, heat to 110 °C, and stir the reaction for 15 hours. Cool to room temperature, add 40 mL of water, separate the organic phase, extract the aqueous phase with ethyl acetate, combine and dry the organic phases, filter, concentrate the filtrate under reduced pressure to dryness to obtain the compound Int-4, a brown solid, which is directly used in the next step without purification, with a yield of 87%.

[0222] Step 4: Preparation of compound Int-5

[0223]

[0224] Under nitrogen protection, mix 20.0 mmol of the compound Int-4 prepared in the previous step, 1.0 mol of triethyl orthoformate and 40.0 mmol of ammonium hexafluorophosphate, heat to 90 °C and stir the reaction for 18 hours. Cool to room temperature, concentrate under reduced pressure to a remaining volume of about 20 mL, add 150 mL of petroleum ether, stir and filter, wash the filter cake with water, and dry in vacuo to obtain the compound Int-5, a gray solid, with a yield of 80%.

[0225] Step 5: Preparation of compound P20 (G = B)

[0226]

[0227] Under nitrogen protection, mix 14.0 mmol of the compound Int-5 prepared in the previous step, 14.0 mmol of Pt(COD)Cl2 and 300 mL of 1,4-dioxane, then add 42.0 mmol of anhydrous sodium acetate, heat to reflux and stir the reaction for 3 days. Cool to room temperature, concentrate to dryness under reduced pressure, disperse in dichloromethane, filter, concentrate the filtrate under reduced pressure to dryness, and purify by silica gel column chromatography to obtain the compound P20 (G = B), a yellow solid, with a yield of 32%; 1HNMR (δ, CDCl3): 8.71 - 8.70 (1H, d); 8.40 - 8.38 (1H, d); 8.34 - 8.32 (1H, d); 8.23 - 8.21 (1H, d); 8.12 - 8.06 (3H, m); 7.98 - 7.92 (3H, m); 7.79 - 7.73 (3H, m); 7.61 - 7.59 (1H, d); 7.49 - 7.44 (3H, m); 7.35 - 7.31 (1H, m); 7.21 - 7.19 (1H, d); 7.01 - 6.95 (3H, m); 6.93 (1H, s); 6.91 - 6.86 (3H, m); 6.75 - 6.73 (1H, d); 1.49 (18H, s); 1.37 (9H, s); 1.32 (9H, s). HRMS: 1825.9513 [M + H], and this product was determined to be the target product.

[0228] Example 3

[0229] The preparation route of metal complex P45 (G = B) is as follows:

[0230]

[0231] Preparation of compound Int-6: Referring to the synthesis method of the first step in Example 2 above, only replace compound A7 in the first step of Example 2 with compound A3 to prepare compound Int-6, a yellow solid with a yield of 80%.

[0232] Preparation of compound Int-7: Referring to the synthesis method of the second step in Example 2 above, only replace compound Int-2 in the second step of Example 2 with compound Int-6 to prepare compound Int-7, a brown solid, without purification, with a yield of 100%.

[0233] Preparation of compound Int-8: Referring to the synthesis method of the third step in Example 2 above, replace compound Int-3 in the third step of Example 2 with compound Int-7, and replace compound PC-1 in the third step of Example 2 with compound PC-2 (CAS: 2307700-01-0) to prepare compound Int-8, a brown solid with a yield of 78%.

[0234] Preparation of compound Int-9: Referring to the synthesis method of the fourth step in Example 2 above, only replace compound Int-4 in the fourth step of Example 2 with compound Int-8 to prepare compound Int-9, a gray solid with a yield of 83%.

[0235] Preparation of metal complex P45 (G = B): Referring to the synthesis method in the fifth step of Example 2 above, only replace the compound Int-5 in the fifth step of Example 2 with compound Int-9 to prepare metal complex P45 (G = B), a yellow solid with a yield of 36%. 1 HNMR (δ, DMSO-d6): 8.54 - 8.52 (1H, d); 8.41 - 8.39 (2H, d); 8.12 - 8.07 (2H, m); 7.98 - 7.96 (2H, d); 7.79 - 7.77 (1H, m); 7.72 - 7.70 (2H, d); 7.59 - 7.57 (2H, d); 7.48 - 7.44 (2H, m); 7.35 - 7.31 (1H, m); 7.21 - 7.16 (2H, m); 7.02 - 6.99 (2H, m); 6.97 - 6.88 (5H, m); 6.77 - 6.75 (1H, d); 6.56 - 6.54 (1H, d); 1.46 (24H, s); 1.35 (9H, s). HRMS: 1202.4442 [M + H], and this product was determined to be the target product.

[0236] Example 4

[0237] The preparation route of metal complex P25 (G = B) is as follows:

[0238]

[0239] Preparation of compound Int-10: Under nitrogen protection, mix 10.0 mmol of compound A7, 12.0 mol of bis(pinacolato)diboron, and 15.0 mmol of anhydrous potassium acetate, then add 0.1 mmol of PdCl2(dppf) and 50 mL of DMF, heat to 90 °C and stir for 15 hours. Cool to room temperature, concentrate under reduced pressure to dryness, dissolve with 100 mL of dichloromethane, wash with water three times, dry the organic phase, filter, concentrate the filtrate under reduced pressure and purify by silica gel column to obtain compound Int-10, a yellow solid, yield: 87%.

[0240] Preparation of compound Int-11: Under nitrogen protection, mix 12.0 mmol of 4-bromopyridine, 10.0 mol of compound Int-10, and 15.0 mmol of anhydrous potassium carbonate, then add 0.01 mmol of Pd132 and 60 mL of THF, heat to reflux and stir for 15 hours. Cool to room temperature, concentrate under reduced pressure to dryness, dissolve with 100 mL of dichloromethane, filter, concentrate the filtrate under reduced pressure and purify by silica gel column to obtain compound Int-11, a brown solid, yield: 76%.

[0241] Preparation of Compound Int-12: Under nitrogen protection, 8.0 mmol of 2-dimethylaminoethanol was dissolved in 10 mL of dry THF. The temperature was lowered to 0 °C, and 16.0 mmol of 2.5 M n-butyllithium in n-hexane solution was added dropwise. The mixture was stirred for 30 minutes. A solution of 2.66 mmol of Compound Int-11 in THF was added dropwise, and the mixture was stirred for 1 hour. The temperature was lowered to -78 °C, and then a solution of 12.7 mmol of carbon tetrabromide in THF was added dropwise, and the mixture was stirred for 1 hour. The temperature was raised to room temperature and stirred for 1 hour. 50 mL of water and 100 mL of dichloromethane were added. The organic phase was separated, the aqueous phase was extracted with dichloromethane, the combined organic phases were washed with water, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain Compound Int-12, a brown solid, with a yield of 82%.

[0242] Preparation of Compound Int-13: Under nitrogen protection, 20.0 mmol of Compound Int-12, 2.0 mmol of cuprous iodide, 22.0 mmol of 3-bromocarbazole, 4.0 mmol of 1-methylimidazole, and 40.0 mmol of lithium tert-butoxide were mixed, and 100 mL of xylene was added. The temperature was raised to reflux, and the mixture was stirred for 48 hours. The temperature was lowered to room temperature, 50 mL of water was added, and the mixture was stirred for 10 minutes. The organic phase was separated, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure and separated and purified by silica gel column chromatography to obtain Compound Int-13, a yellow solid, with a yield of 90%.

[0243] Preparation of Compound Int-14: Under nitrogen protection, 20.0 mmol of Compound Int-13, 24.0 mmol of m-chlorophenol, 40.0 mmol of anhydrous potassium phosphate, and 2.0 mmol of cuprous iodide were mixed. Then 4.0 mmol of 2-pyridinecarboxylic acid and 50 mL of dry DMSO were added. The temperature was raised to 110 °C and stirred for 48 hours. The temperature was lowered to room temperature, the reaction solution was poured into 250 mL of ice water, stirred for 30 minutes, extracted with ethyl acetate, the organic phase was washed with saturated brine, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure and separated and purified by silica gel column chromatography to obtain Compound Int-14, a yellow solid, with a yield of 74%.

[0244] Preparation of Compound Int-15: Referring to the synthesis method of the third step of Example 2 above, Compound Int-3 in the third step of Example 2 was replaced with Compound sub-1( R B18 is ), and Compound PC-1 in the third step of Example 2 was replaced with Compound Int-14 to prepare Compound Int-15, a brown solid, with a yield of 85%.

[0245] Preparation of Compound Int-16: Referring to the synthesis method in the fourth step of Example 2 above, only replace Compound Int-4 in the fourth step of Example 2 with Compound Int-15 to prepare Compound Int-16, a brown solid with a yield of 82%.

[0246] Preparation of Metal Complex P25 (G = B): Referring to the synthesis method in the fifth step of Example 2 above, only replace Compound Int-5 in the fifth step of Example 2 with Compound Int-16 to prepare Metal Complex P25 (G = B), an orange solid with a yield of 42%; 1 HNMR (δ, CDCl3): 8.56 - 8.54 (1H, d); 8.31 - 8.29 (1H, d); 8.11 - 8.06 (3H, m); 8.02 - 7.89 (5H, m); 7.85 - 7.82 (1H, m); 7.77 - 7.73 (2H, t); 7.52 - 7.44 (5H, m); 7.35 - 7.31 (1H, m); 7.20 - 7.16 (1H, m); 7.11 (1H, s); 7.04 - 6.96 (4H, m); 6.94 - 6.87 (4H, m); 6.77 - 6.75 (1H, d); 6.57 - 6.55 (1H, m); 1.46 (18H, s); 1.32 (18H, s). HRMS: 1282.5068 [M + H], and this product was determined to be the target product.

[0247] Example 5

[0248] Preparation of Metal Complex P49 (G = N) includes the following steps:

[0249] The first step: Preparation of Compound B1

[0250]

[0251] Under nitrogen protection, 10.0 mmol of 4-chloro-2,6-dibromoaniline, 40.0 mmol of 1,1,2,2-tetramethyl-6-bromo-5-acenaphtheneboric acid, 60.0 mmol of anhydrous potassium carbonate, and 2.0 mmol of Pd(PPh3)4 were mixed, then 50 mL of toluene, 20 mL of ethanol, and 10 mL of water were added, and the temperature was raised to reflux and stirred for 24 hours. 50 mL of water was added to the reaction solution, and it was extracted with ethyl acetate. The organic phase was dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and purified by silica gel column chromatography to obtain Compound B1, a yellow solid with a yield of 67%.

[0252] The second step: Preparation of Compound Int-17

[0253]

[0254] Under nitrogen protection, 14.0 mmol of compound PC-3 (CAS: 2996139-02-5), 16.8 mmol of 2-chloro-3-nitropyridine, 28.0 mmol of N,N-diisopropylethylamine and 50 mL of DMSO were heated to 100 °C and stirred for reaction for 36 hours, then cooled to room temperature. 150 mL of ethyl acetate was added, washed with saturated brine, the organic phase was dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified by silica gel column to obtain compound Int-17, a brown solid, with a yield of 69%.

[0255] Step 3: Preparation of compound Int-18

[0256]

[0257] Referring to the synthesis method of the second step of Example 2 above, only replacing compound Int-2 in the second step of Example 2 with compound Int-17, compound Int-18 was obtained, a yellow solid, without purification, directly used for the next step reaction, with a yield of 100%.

[0258] Step 4: Preparation of compound Int-19

[0259]

[0260] Under nitrogen protection, 10.0 mmol of compound B1, 11.0 mmol of compound Int-18, 15.0 mmol of sodium tert-butoxide, 0.1 mmol of Pd2(dba)3 and 80 mL of toluene were mixed, then 0.2 mmol of Xantphos was added, heated to 110 °C, and stirred for reaction for 15 hours. Cooled to room temperature, 50 mL of water was added, the organic phase was separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined and washed with saturated brine, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain intermediate Int-19, a brown solid, without purification, directly used for the next step reaction, yield: 74%.

[0261] Step 5: Preparation of compound Int-20

[0262]

[0263] Referring to the synthesis method of the fourth step of Example 2 above, only replacing compound Int-4 in the fourth step of Example 2 with compound Int-19, compound Int-20 was prepared, a gray solid, with a yield of 78%.

[0264] Step 6: Preparation of metal complex P49 (G = N)

[0265]

[0266] Referring to the synthesis method of the fifth step of Example 2 above, only replace the compound Int-5 in the fifth step of Example 2 with the compound Int-20 to prepare the metal complex P49 (G = N), a yellow solid with a yield of 35%; 1 HNMR (δ, CDCl3): 8.92 - 8.90 (1H, d); 8.66 - 8.64 (2H, d); 8.15 - 8.13 (1H, m); 7.82 - 7.80 (1H, m); 7.78 (2H, s); 7.69 - 7.67 (1H, d); 7.52 - 7.45 (4H, m); 7.41 - 7.39 (3H, m); 7.35 - 7.31 (2H, m); 7.24 - 7.20 (1H, m); 7.10 - 7.08 (1H, m); 7.05 - 7.02 (1H, m); 7.00 - 6.95 (3H, m); 6.92 - 6.90 (1H, m); 6.67 - 6.65 (1H, d); 1.37 (24H, s); 1.31 (9H, s). HRMS: 1206.4334 [M + H], and this product was determined to be the target product.

[0267] Example 6

[0268] Preparation of the metal complex P61 (G = N) includes the following steps:

[0269] First step: Preparation of compound B2

[0270]

[0271] Referring to the synthesis method of the first step of Example 5 above, only replace 1,1,2,2 - tetramethyl - 6 - bromo - 5 - acenaphtheneboronic acid in the first step of Example 5 with 8 - chloro - 9 - phenanthreneboronic acid to prepare compound B2, a white solid with a yield of 48%.

[0272] Second step: Preparation of the metal complex P61 (G = N)

[0273]

[0274] Prepare compound Int - 21: Referring to the synthesis method of the first step of Example 2 above, only replace the compound A7 in the first step of Example 2 with compound B2 to prepare compound Int - 21, a yellow solid with a yield of 86%.

[0275] Prepare compound Int - 22: Referring to the synthesis method of the second step of Example 2 above, only replace the compound Int - 2 in the second step of Example 2 with compound Int - 21 to prepare compound Int - 22, a yellow solid, without purification, with a yield of 100%.

[0276] Preparation of Compound Int-23: Referring to the synthesis method of the third step in Example 2 above, replace Compound Int-3 in the third step of Example 2 with Int-22, and replace Compound PC-1 in the third step of Example 2 with Compound PC-2 to prepare Compound Int-23, which is a brown solid with a yield of 76%.

[0277] Preparation of Compound Int-24: Referring to the synthesis method of the fourth step in Example 2 above, only replace Compound Int-4 in the fourth step of Example 2 with Compound Int-23 to prepare intermediate Compound Int-24, which is a grey solid with a yield of 77%.

[0278] Preparation of Complex P61 (G = N): Referring to the synthesis method of the fifth step in Example 2 above, only replace Compound Int-5 in the fifth step of Example 2 with Compound Int-24 to prepare metal complex P61 (G = N), which is a yellow solid with a yield of 52%; 1 HNMR (δ, CDCl3): 8.91 - 8.89 (1H, d); 8.69 (2H, s); 8.63 (2H, s); 8.15 - 8.13 (1H, m); 8.03 - 7.98 (2H, m); 7.92 (2H, s); 7.82 - 7.80 (1H, m); 7.69 - 7.62 (5H, m); 7.52 (2H, s); 7.48 - 7.43 (3H, m); 7.41 (1H, s); 7.35 - 7.31 (2H, m); 7.18 - 7.14 (1H, m); 7.06 - 7.01 (3H, m); 6.98 - 6.94 (1H, m); 6.92 - 6.87 (3H, m); 6.85 - 6.83 (2H, m); 1.32 (9H, s). HRMS: 1141.3139 [M + H], and this product is determined to be the target product.

[0279] Preparation of the Organic Electroluminescent Device in Example 7

[0280] Ultrasonically treat the glass substrate with the patterned ITO electrode in a cleaning agent for 30 minutes, rinse it in deionized water, ultrasonically treat it in an acetone / ethanol mixed solvent for 30 minutes, and 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.

[0281] Place the above-treated ITO glass substrate in a vacuum chamber and evacuate it to less than 1×10 -5 Pa, and deposit metallic silver as the anode on the above ITO film, with the deposited film thickness being Continue to deposit Compound HATCN as the hole injection layer, with the deposited film thickness being Continue to deposit Compound HTM as the hole transport layer on the above hole injection layer film, with the deposited film thickness being

[0282] Compound BPrime is evaporated on the above hole transport layer as an electron blocking layer, and the evaporation film thickness is

[0283] The metal complex of the present invention, compound H1, and compound H2 are evaporated on the above electron blocking layer as the organic light emitting layer of the device. Among them, compound H1 and compound H2 are host materials, and the mass ratio of compound H1 to H2 is 1:1. The metal complex of the present invention is a doping material, and the doping mass concentration is 12%. The evaporation film thickness is

[0284] Another layer of compound DPO is evaporated on the above organic light emitting layer as the hole blocking layer of the device, and the evaporation film thickness is

[0285] Another layer of LiQ and compound ET018 is evaporated on the above hole blocking layer as the electron transport layer of the device. Among them, LiQ is 50% of the mass of compound ET018, and the evaporation film thickness is

[0286] Another layer of LiF is evaporated on the above electron transport layer as the electron injection layer of the device, and the evaporation film thickness is

[0287] Metal magnesium and silver are evaporated on the above electron injection layer as the cathode layer of the device. Among them, the mass ratio of magnesium to silver is 1:10, and the evaporation film thickness is

[0288] Finally, compound HTM is evaporated on the cathode layer as the capping layer, and the evaporation film thickness is Fabricate the organic electroluminescent element of the present invention, as shown in the attached Figure 1 Device 100.

[0289] Comparative Example 1

[0290] Compound BD012 is used to replace the metal complex of the above organic electroluminescent device, and the other steps are the same as those in Example 7 to fabricate Comparative Element 1.

[0291] The structural formulas of the aforementioned compounds HATCN, HTM, BPrime, H1, H2, BD012, DPO, and ET018 are as follows:

[0292]

[0293] For the above-prepared organic electroluminescent device, a digital source meter and a luminance meter were used to measure the driving voltage, current efficiency, and the lifetime of the device. Specifically, the voltage was increased at a rate of 0.1 V per second, and the voltage when the current density of the organic electroluminescent device reached 10 mA / cm 2 was measured as the driving voltage, and the luminance at this time was also measured; the ratio of the luminance to the current density was the current efficiency; the LT95% lifetime test was as follows: using a luminance meter at a luminance of 1000 cd / m 2 , maintaining a constant current, and measuring the time it took for the luminance of the organic electroluminescent device to decay to 950 cd / m 2 . The unit was hours, and some of the test results were summarized in Table 1. *The data was normalized compared to Comparative Element 1.

[0294] Table 1

[0295]

[0296]

[0297]

[0298] As can be seen from Table 1, compared with Comparative Element 1, the organic electroluminescent device prepared with the metal complex of the present invention has a lower driving voltage, higher luminous efficiency, and excellent lifetime, and is an organic electroluminescent material with excellent performance.

[0299] Compared with the metal complex BD012 of Comparative Element 1, the metal complex of the present invention is different in that during the metal-to-ligand charge transfer process of C^Pt^N in the metal complex of the present invention, the sterically bulky groups of the boron-containing fused ring and the nitrogen-containing fused ring are used to enhance the steric hindrance and polarity in the direction of metal polarization, and the bonding strength of the C-N bond in the ligand is increased, thereby improving the stability of the metal complex. Therefore, the metal complex disclosed in the present application has a low driving voltage, high efficiency, and excellent device lifetime performance.

[0300] As described above, only the representative examples of the specific embodiments of the present invention are given, 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 should be covered within the protection scope of the present invention. Therefore, the protection scope of the present invention should be subject to the protection scope of the claimed rights.

Claims

1. A metal complex, characterized in that, The metal complex comprises the structure of formula (1): Wherein, ring A, ring B, ring C and ring D are each independently selected from a monocyclic or polycyclic fused ring, wherein each ring of the monocyclic and polycyclic fused ring is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring, and at least one substituent R is included in ring A, ring B, ring C and ring D x , said R x is a structure represented by formula (2): M represents a metal element with an atomic weight greater than 40; X 1 ~X 6 Each independently selected from C, B or N; Z 1 to Z 4 Each independently selected from C or N, Z 5 to Z 19 Each independently selected from CH or N; and among Z 5 、Z 6 、Z 7 at least one is CH; G is selected from B, N or P; Y 1 、Y 2 、L 1 、L 2 each independently selected from a single bond, O, S, S═O, SO2, Se, NR 3 、PR 4 、R 4 P═O, CR 4 R 5 、C═O, SiR 4 R 5 、GeR 4 R 5 or BR 4 ; provided that at least one of L 1 、L 2 is selected from NR 4 、PR 4 、R 4 P═O, CR 4 R 5 、SiR 4 R 5 、GeR 4 R 5 or BR 4 and at least one of L 1 、L 2 is fused or joined to the ring to which it is attached to form a ring; R 1 、R 2 、R 3 、R a 、R b 、R c and R d each represents mono-substituted, di-substituted or multi-substituted up to fully saturated substitution, or unsubstituted; R a 、R b 、R c 、R d 、R 1 ~R 5 are each independently selected from formula (2), or selected from the group consisting of: hydrogen, deuterium, a halogen atom, a nitrile group, an acyl group, a carboxyl group, an ether group, an ester group, an isonitrile group, a sulfur group, a selenoalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, a substituted or unsubstituted C1-C 40 linear alkyl group, a substituted or unsubstituted C1-C 40 linear heteroalkyl group, a substituted or unsubstituted C3-C 40 branched or cyclic alkyl group, a substituted or unsubstituted C1-C 40 alkoxy group, a substituted or unsubstituted C6-C 60 arylalkyl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylamino group, a substituted or unsubstituted C3-C 40 silyl group, a substituted or unsubstituted C2-C 40 alkenyl group, a substituted or unsubstituted C4-C 40 cycloalkenyl group, a substituted or unsubstituted C2-C 40 heteroalkenyl group, a substituted or unsubstituted C2-C 40 alkynyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C2-C 60 heteroaryl group and combinations thereof, optionally, any two or more adjacent R a 、R b 、R c 、R d 、R 1 ~R 5 may optionally be joined or fused to form a substituted or unsubstituted ring; When substituted, the substituents are each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxyl group or its carboxylate, a sulfonic acid group or its sulfonate, a phosphoric acid group or its phosphate, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C1-C 40 alkoxy group, a C3-C 40 cycloalkyl group, a C3-C 40 cycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthioether group, and a C2-C 60 heteroaryl group, or a combination of any one or at least two of them; represents the substituent R x the connection positions with rings A, B, C and D 2. The metal complex according to claim 1, wherein The metal complex has a group of compounds with the composition of formula M(LA)(LB): wherein, LA-LB is selected from the group consisting of: and / or LA-LB is selected from the group consisting of: Among them, W is selected from O, S, CR 6 R 7 , SiR 6 R 7 , CR 6 R 7 -CR 8 R 9 or NR Y ; Y is selected from O, S or NR Y ; Each R Y is the same or different and is independently selected from formula (2) or the group consisting of: substituted or unsubstituted C1-C 40 linear alkyl, substituted or unsubstituted C3-C 40 branched or cyclic alkyl, substituted or unsubstituted C6-C 60 arylalkyl, substituted or unsubstituted C2-C 40 alkenyl, substituted or unsubstituted C4-C 40 cycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl and combinations thereof, optionally, R Y may be joined or fused with adjacent R a , R c or R d to form, optionally, a substituted or unsubstituted ring; R 6 to R 9 each independently selected from hydrogen, or a group consisting of: deuterium, a halogen atom, a nitrile group, an acyl group, a carboxyl group, an ether group, an ester group, an isonitrile group, a sulfur group, a selenoalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, a substituted or unsubstituted C1-C 40 linear alkyl, a substituted or unsubstituted C1-C 40 linear heteroalkyl, a substituted or unsubstituted C3-C 40 branched or cyclic alkyl, a substituted or unsubstituted C1-C 40 alkoxy, a substituted or unsubstituted C6-C 60 arylalkyl, a substituted or unsubstituted C6-C 60 aryloxy, a substituted or unsubstituted C6-C 60 arylamino, a substituted or unsubstituted C3-C 40 silyl, a substituted or unsubstituted C2-C 40 alkenyl, a substituted or unsubstituted C4-C 40 cycloalkenyl, a substituted or unsubstituted C2-C 40 heteroalkenyl, a substituted or unsubstituted C2-C 40 alkynyl, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C2-C 60 heteroaryl and combinations thereof, optionally, any two or more adjacent R 6 to R 9 may optionally be joined or fused to form a substituted or unsubstituted ring; When substituted, the substituents are each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxyl group or its carboxylate, a sulfonic acid group or its sulfonate, a phosphoric acid group or its phosphate, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C1-C 40 alkoxy group, a C3-C 40 cycloalkyl group, a C3-C 40 cycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthioether group, and a C2-C 60 heteroaryl group, or a combination of any one or at least two of them.

3. The metal complex according to claim 1 or 2, characterized in that, M is selected from Ir, Pt, Pd, Ru, Rh, Os, Au, Cu, Ni, Co, Ga or Ge; G is selected from B or N; L 1 and L 2 each independently selected from a single bond, O, S, Se, NR 4 , PR 4 , BR 4 , CR 4 R 5 or SiR 4 R 5 ; Y 1 and Y 2 each independently selected from a single bond, O or S; Z 5 ~Z 19 are all CH, or Z 5 and Z 7 -Z 19 are all CH, Z 6 is N; W is selected from O, S, C(CH3)2, C(C6H5)2, Si(CH3)2, Si(C6H5)2 or NR Y ; Y is independently selected from O, S or NR Y ; R Y selected from substituted or unsubstituted C1-C 40 linear alkyl, substituted or unsubstituted C1-C 40 linear heteroalkyl, substituted or unsubstituted C3-C 40 branched or cyclic alkyl, substituted or unsubstituted C1-C 40 heterocyclic alkyl, substituted or unsubstituted C1-C 40 alkoxy, substituted or unsubstituted C6-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylamino, substituted or unsubstituted C1-C 40 alkylamino, substituted or unsubstituted C3-C 40 silyl, substituted or unsubstituted C3-C 60 arylsilyl, 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 heteroaryl and combinations thereof; When substituted, the substituents are each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxyl group or its carboxylate, a sulfonic acid group or its sulfonate, a phosphoric acid group or its phosphate, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C1-C 40 alkoxy group, a C3-C 40 cycloalkyl group, a C3-C 40 cycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthioether group, and a C2-C 60 heteroaryl group, or a combination of any one or at least two thereof.

4. The metal complex according to any one of claims 1 to 3, characterized in that, M is selected from Pt or Pd; R a 、R b 、R c 、R d are each independently selected from formula (2) or the group consisting of a hydrogen atom, a deuterium atom, fluorine, a cyano group, an isocyano group, R A1 ~R A30 、R B1 ~R B195 、R C1 ~R C80 ; The R x is selected from the group consisting of formula (3), formula (4), formula (5) or formula (6): R 1 、 R 2 、 R 3 each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, R A1 to R A30 、 R B1 to R B195 、 R C1 to R C80 ; R 4 ~R 9 Each independently selected from the group consisting of a hydrogen atom, R A1 ~R A25 , R B1 ~R B185 , R C1 ~R C79 ; R Y Each independently selected from formula (2) or the group consisting of R A1 ~R A25 、R B1 ~R B185 、R C1 ~R C79 at each occurrence; Among them, R A1 ~R A30 The structural formulas are shown as follows: R B1 ~R B195 The structure shown is as follows: R C1 ~R C80 The structure shown is as follows: wherein each hydrogen atom in each substituent can be partially or completely replaced by a deuterium atom.

5. The metal complex according to any one of claims 1 to 4, characterized in that, Said Y 1 and Y 2 and L 1 are each O; L 2 is selected from O, NR 4 , PR 4 or BR 4 ; Y is each NR Y ; W is selected from O, S, C(CH3)2, C(C6H5)2, Si(CH3)2 or Si(C6H5)2.

6. The metal complex according to any one of claims 1 to 5, characterized in that, The metal complex is selected from the structures shown by the following formula, wherein at least one substituent R in the structure shown by the following formula x substitutes: Among them, R x , R a , R b , R c , R d has the definition described in any one of claims 1-5; Preferably, R a , R b , R c , R d are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, an isonitrile group, R A1 to R A30 , R B1 to R B195 , R C1 to R C80 . Preferably, R x is selected from the group consisting of formula (3), formula (4), formula (5) or formula (6): R 1 、R 2 、R 3 each independently is selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, R A1 to R A30 、R B1 to R B195 、R C1 to R C80 ; optionally, any two or more adjacent R 1 -R 5 may be optionally joined or fused to form a substituted or unsubstituted ring; optionally, the ring is substituted with one or more substituents selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C10 cycloalkyl group, a C6-C10 aryl group, and a C2-C10 heteroaryl group.

7. The metal complex according to any one of claims 1-6, characterized in that, The metal complex is selected from the group consisting of: wherein, G is selected from B or N.

8. An organic electroluminescent device, the organic electroluminescent device includes an anode, a cathode and an organic layer disposed between the anode and the cathode, and the organic layer includes the metal complex according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic layer further includes a host material and a doping material, the doping material includes the metal complex according to any one of claims 1 to 7; the host material is selected from the group consisting of triphenylene, carbazolyl, indolocarbazolyl, dibenzothiophenyl, dibenzofuranyl, fluorenyl, dibenzoselenophenyl, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracenyl, aza-triphenylene, aza-carbazolyl, aza-indolocarbazolyl, aza-dibenzothiophenyl, aza-dibenzofuranyl, aza-dibenzoselenophenyl and aza-(5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene)yl or a combination derived from these systems.

10. A consumer product comprising the organic electroluminescent device according to claim 8 or 9.

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