Metal organic complex and application thereof

Abstract

The invention provides a metal organic complex and application thereof. The metal organic complex comprises a metal atom M and a first ligand La coordinated with the metal atom M. The structure of the first ligand La is as shown in formula (I). The metal organic complex provided by the invention can be used for preparing an organic electroluminescent device with high purity, high brightness and high efficiency. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescent display, and specifically discloses a metal-organic complex and its application in an organic electroluminescent device. Background Art

[0002] In 1987, Tang et al. from Eastman Kodak Company in the United States first reported a green electroluminescent device made of a double-layer organic thin film. The device uses indium tin oxide (ITO) as the anode, and a 75-nm-thick amorphous and pinhole-free aromatic diamine thin film is evaporated on the anode as the hole transport layer. Then, a 60-nm-thick aluminum tris(8-hydroxyquinoline) thin film is deposited on the aromatic diamine thin film as the electron transport layer and the light-emitting layer, and magnesium-silver alloy is used as the cathode. This double-layer film structure successfully reduces the turn-on voltage to 5.5 V, achieving high-radiance light emission (>1000 cd·m -2 ), with a wavelength of 550 nm and an external quantum efficiency of 1.0%, which has great practical significance. In 1994, Kido et al. from Japan first prepared an organic electroluminescent device that emits white light. They doped three fluorescent dyes of blue, green, and orange in a poly(N-vinylcarbazole) (PVK) thin film as the hole transport layer and the emission layer, used 1,2,4-triazole derivative (TAZ) as the hole blocking layer, and aluminum tris(8-hydroxyquinoline) (Alq 3 ) as the electron transport layer. The device composition is: glass substrate / ITO / PVK / TAZ / Alq 3 / Mg:Ag multi-layer structure. At a driving voltage of 14 V, white light emission with a wide coverage of the visible light region and a brightness as high as 3400 cd·m -2 is obtained. This high-brightness white emission is achieved by doping fluorescent compounds of multiple colors in a polymer thin film to form a single light-emitting layer. This discovery by Kido et al. has added a significant touch to the application of organic electroluminescence, opened the door for organic light-emitting devices in the lighting field, and promoted the further development of organic light-emitting devices.

[0003] The light emitted by an organic electroluminescent device is also divided into fluorescence and phosphorescence. The light emitted by the energy of singlet excitons is fluorescence, while the light emitted by the energy of both singlet and triplet excitons is phosphorescence. Since the ratio of the number of singlet and triplet excitons formed is a fixed value of 1:3, theoretically, the highest internal quantum efficiency of a fluorescence device that only utilizes singlet excitons is only 25%, while on the contrary, the internal quantum efficiency when emitting phosphorescence can reach 100%.

[0004] At present, organometallic complexes with phosphorescent emission and organic electroluminescent devices have both been reported, and a variety of organometallic complex phosphorescent materials have also been disclosed in patents. For example, a class of Ir complexes containing pyridine and dibenzofuran ligands is disclosed in the US patent of EP3825320A1. However, due to the serious problems of low phosphorescence efficiency, poor stability and short lifespan of these compounds, their commercialization potential has been hindered. Summary of the Invention

[0005] The object of the present invention is to develop an organometallic complex and apply it to an organic electroluminescent device, so that the prepared electroluminescent device exhibits excellent properties of high purity, high brightness and high efficiency.

[0006] Specifically, in a first aspect, the present invention provides an organometallic complex, which includes a metal atom M and a first ligand L coordinated with the metal atom M a , wherein the first ligand L a has a structure shown in formula (Ⅰ):

[0007]

[0008] In formula (I), R 1 , R 2 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 straight-chain or branched-chain alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and R 1 , R 2 are either not connected or connected by a chemical bond to form a ring;

[0009] Z 1 -Z 4 are each independently selected from CR Z or N;

[0010] U 1 -U 4 are each independently selected from C, CR U1 or N, and any two adjacent ones in U 1 -U 4 are C and fused with formula (I-a) to form a ring; in formula (I-a), represents the connection site with formula (I); U 5 -U 8 are each independently selected from CR U2 or N; X is selected from CRx 1 Rx 2 , NRx3 、SiRx 4 Rx 5 、 any one of S, O or Se;

[0011] The R Z 、R U1 、R U2 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, hydroxy, ester, amino, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy; any two adjacent Rs Z are not connected or are connected by a chemical bond to form a ring; any two adjacent Rs U1 are not connected or are connected by a chemical bond to form a ring; any two adjacent Rs U2 are not connected or are connected by a chemical bond to form a ring;

[0012] The Rx 1 、Rx 2 、Rx 3 、Rx 4 、Rx 5 are each independently selected from hydrogen, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and any two of the Rx 1 、Rx 2 or Rx 4 、Rx 5 are not connected or are connected by a chemical bond to form a ring;

[0013] R 1 、R 2 、R Z 、R U1 、R U2 、Rx 1 、Rx 2 、Rx 3 、Rx 4 、Rx 5When there is one or more substituents, the substituents are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 linear or branched alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, C3-C30 heteroaryl, or any combination of at least two of them; when there are multiple substituents, any two adjacent substituents are not connected or are connected by a chemical bond to form a ring;

[0014] The dashed line represents the ligand L a The binding site with the metal atom M;

[0015] n is 1, 2, 3, 4, 5, 6, 7 or 8.

[0016] The metal-organic complex of the present invention contains a ligand having the structure shown in the above formula (I), and its parent nucleus contains a special ring structure and connection sites, making the metal-organic complex have suitable conjugation properties, improving the energy levels of the molecules. When it is used in an OLED, especially when used in a red light-emitting layer, it can significantly improve the luminescence efficiency and lifespan.

[0017] In some embodiments, the first ligand L a has the structure shown in any one of formulas (Ⅰ-1) - (Ⅰ-6):

[0018]

[0019] Wherein, R 1 , R 2 , Z 1 -Z 4 , U 1 -U 8 , X, and n are defined the same as in formula (Ⅰ).

[0020] In some preferred embodiments, n is selected from any integer from 1 to 6 (such as 2, 3, 4, 5, etc.). In the present invention, when n is greater than or equal to 2 (such as 3, 4, 5, etc.), multiple R 1 are the same or different groups; multiple R 2 are the same or different groups. In some preferred embodiments, n is selected from 1, 2 or 3.

[0021] In some preferred embodiments, R 1 , R 2Each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl.

[0022] In some embodiments, R 1 、R 2 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 straight-chain or branched-chain alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl.

[0023] In some embodiments, R 1 、R 2 Each independently selected from hydrogen, deuterium, or any one of the following substituted or unsubstituted groups: C1-C6 straight-chain or branched-chain alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C12 aryl, C3-C12 heteroaryl.

[0024] In some embodiments, R 1 、R 2 Each independently selected from hydrogen, deuterium, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, methoxy, ethoxy, -O-propyl, -O-isopropyl, -O-butyl, -O-tert-butyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, pyrrolidinyl, tetrahydropyranyl, phenyl, naphthyl, biphenyl, pyridyl, furyl, thienyl.

[0025] In some embodiments, when R1 and R 2 when contains one or more substituents, each of the substituents is independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 straight-chain or branched-chain alkyl, C3-C6 cycloalkyl, C6-C10 aryl, and C3-C10 heteroaryl. In some embodiments, when R 1 and R 2 contains one or more substituents, each of the substituents is independently selected from deuterium, fluorine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, or phenyl. In some examples, R 1 and R 2 contains 1-9 substituents. In some examples, R 1 and R 2 contains 1-6 substituents. In some examples, R 1 and R 2 contains 1-3 substituents. In the present invention, when R 1 and R 2 contains more than 2 substituents, any two adjacent substituents are not connected or are connected by a chemical bond to form a 5-6 membered ring.

[0026] In some embodiments, R 1 and R 2 are each independently selected from hydrogen, deuterium, or any one of the following groups:

[0027]

[0028] In some embodiments, R 1 and R 2 are each independently selected from hydrogen, deuterium, deuterated C1-C6 straight-chain or branched-chain alkyl, and C1-C6 straight-chain or branched-chain alkyl. In some embodiments, R 1 and R 2 are each independently selected from hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, propyl, deuterated propyl, isopropyl, deuterated isopropyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, neopentyl, deuterated neopentyl, isopentyl, or deuterated isopentyl.

[0029] In some embodiments, at least one (such as 1, 2, etc.) of R 1 and R 2 is not selected from hydrogen.

[0030] In some embodiments, at most 1 (0 or 1) of Z 1 -Z 4 is selected from N, and the rest are selected from CR Z , and multiple (such as 2, 3, 4) RZ are the same or different groups. In some embodiments, Z 1 -Z 4 are each independently selected from CR Z . In some embodiments, Z 1 , Z 2 , Z 4 are selected from CH, and Z 3 is selected from CR Z . In some embodiments, Z 1 -Z 4 are both CH.

[0031] In some embodiments, the R Z are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryloxy.

[0032] In some embodiments, the R Z are each independently selected from hydrogen, deuterium, a halogen, cyano, a substituted or unsubstituted C1-C10 straight-chain or branched alkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C1-C10 alkylsilyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 heterocycloalkyl, a substituted or unsubstituted C6-C20 aryl, a substituted or unsubstituted C3-C20 heteroaryl, a substituted or unsubstituted C6-C20 arylamino, or a substituted or unsubstituted C3-C20 heteroarylamino.

[0033] In some embodiments, the R Z are each independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following substituted or unsubstituted groups: C1-C6 straight-chain or branched alkyl, C1-C6 alkoxy, C1-C6 alkylsilyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C15 aryl, C3-C15 heteroaryl, C6-C15 arylamino, C3-C15 heteroarylamino.

[0034] In some embodiments, the R Z are each independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, methoxy, ethoxy, -O-propyl, -O-isopropyl, -O-butyl, -O-tert-butyl, trimethylsilyl, di(ethyl)methylsilyl, triethylsilyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, pyrrolidinyl, tetrahydropyranyl, phenyl, naphthyl, biphenyl, fluorenyl, 9,9-dimethylfluorenyl, pyridyl, furyl, thienyl, dibenzofuran, dibenzothiophene, carbazolyl, diphenylamino, dipyridylamino.

[0035] In some embodiments, when R Z contains one or more substituents, the substituents are each independently selected from deuterium, a halogen, cyano, a C1-C6 (such as C2, C3, C4, C5, etc.) straight-chain or branched alkyl, a C3-C6 (such as C4, C5, etc.) cycloalkyl, a C6-C10 (such as C6, C9, C10) aryl, or a C3-C10 (such as C3, C4, C5, C6, C9, C10) heteroaryl, or a combination of any one or at least two of them.

[0036] In some embodiments, when R Z contains one or more substituents, the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, or phenyl.

[0037] In some embodiments, when there are more than two substituents in R Z any two adjacent substituents are not connected or are connected by a chemical bond to form a 5- to 6-membered ring.

[0038] In some embodiments, R Z is selected from hydrogen, deuterium, fluorine, cyano, or any one of the following groups:

[0039]

[0040]

[0041] In some embodiments, any two adjacent Rz are not connected or are connected by a chemical bond to form a ring (for example, forming etc., the dotted line represents a fused bond).

[0042] In some embodiments, in formula (I-1) and formula (I-2), U 3 -U 4 are each independently selected from CR U1 or N. In some embodiments, in formula (I-1) and formula (I-2), U 3 is selected from CR U1 or N, and U 4 is selected from CR U1 . In some embodiments, in formula (I-1) and formula (I-2), U 3 -U 4 are each independently selected from CR U1 , and the two Rs U1 are the same or different groups. In some embodiments, in formula (I-1) and formula (I-2), U 3 is selected from CR U1 , and U 4 is selected from CH.

[0043] In some embodiments, in formula (I-3) and formula (I-4), U 1 and U 4 are each independently selected from CR U1 or N. In some embodiments, in formula (I-3) and formula (I-4), U 1 is selected from CR U1 or N, and U 4 is selected from CR U1 . In some embodiments, in formula (I-3) and formula (I-4), U 1 and U 4 are each independently selected from CR U1 , and the two Rs U1are the same or different groups. In some embodiments, in Formula (I-3) and Formula (I-4), U 1 , U 4 is selected from CH.

[0044] In some embodiments, in Formula (I-5) and Formula (I-6), U 1 , U 2 are each independently selected from CR U1 or N. In some embodiments, in Formula (I-5) and Formula (I-6), U 1 is selected from CR U1 or N, and U 2 is selected from CR U1 . In some embodiments, in Formula (I-5) and Formula (I-6), U 1 , U 2 are each independently selected from CR U1 , and the two R U1 are the same or different groups. In some embodiments, in Formula (I-5) and Formula (I-6), U 1 , U 2 are selected from CH.

[0045] In some embodiments, the R U1Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryloxy.

[0046] In some embodiments, the R U1 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 straight-chain or branched-chain alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C3-C20 heteroarylamino.

[0047] In some embodiments, the R U1Each independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following substituted or unsubstituted groups: C1-C6 linear or branched alkyl, C1-C6 alkoxy, C1-C6 alkylsilyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C15 aryl, C3-C15 heteroaryl, C6-C15 arylamino, C3-C15 heteroarylamino.

[0048] In some embodiments, the R U1 Each independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, methoxy, ethoxy, -O-propyl, -O-isopropyl, -O-butyl, -O-tert-butyl, trimethylsilyl, di(ethyl)methylsilyl, triethylsilyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, pyrrolidinyl, tetrahydropyranyl, phenyl, naphthyl, biphenyl, fluorenyl, 9,9-dimethylfluorenyl, pyridyl, furyl, thienyl, dibenzofuran, dibenzothiophene, carbazolyl, diphenylamino, dipyridylamino.

[0049] In some embodiments, R U1 When containing one or more substituents, the substituents are each independently selected from deuterium, halogen, cyano, C1-C6 (such as C2, C3, C4, C5, etc.) linear or branched alkyl, C3-C6 (such as C4, C5, etc.) cycloalkyl, C6-C10 (such as C6, C9, C10) aryl, C3-C10 (such as C3, C4, C5, C6, C9, C10) heteroaryl, or any combination of at least two of them. In some embodiments, when R U1 When containing one or more substituents, the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl or phenyl. In some embodiments, when R U1 When containing two or more substituents, any two adjacent substituents are not connected or are connected by a chemical bond to form a 5-6 membered ring.

[0050] In some embodiments, R U1 Is selected from hydrogen, deuterium, fluorine, cyano, or any one of the following groups:

[0051]

[0052] In some embodiments, in formula (I-1), formula (I-2), formula (I-5), formula (I-6), any two adjacent R U1 Are not connected or are connected by a chemical bond to form a ring (such as forming etc., the dashed lines represent fused bonds).

[0053] In some embodiments, U 5 -U 8 has at most 1 (e.g., 0 or 1) selected from N, and the rest are selected from CR U2 , and a plurality (e.g., 2, 3, 4) of R U2 are the same or different groups. In some embodiments, U 5 -U 8 are each independently selected from CR U2 . Preferably, no two adjacent R U2 are connected to each other.

[0054] In some embodiments, the R U2Independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryloxy.

[0055] In some embodiments, the R U2 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C3-C20 heteroarylamino.

[0056] In some embodiments, the R U2Independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following substituted or unsubstituted groups: C1-C6 straight or branched alkyl, C1-C6 alkoxy, C1-C6 alkylsilyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C15 aryl, C3-C15 heteroaryl, C6-C15 arylamino, C3-C15 heteroarylamino.

[0057] In some embodiments, R U2 Independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, methoxy, ethoxy, -O-propyl, -O-isopropyl, -O-butyl, -O-tert-butyl, trimethylsilyl, di(ethyl)methylsilyl, triethylsilyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, pyrrolidinyl, tetrahydropyranyl, phenyl, naphthyl, biphenyl, fluorenyl, 9,9-dimethylfluorenyl, pyridyl, furyl, thienyl, dibenzofuran, dibenzothiophene, carbazolyl, diphenylamino, dipyridylamino.

[0058] In some embodiments, R U2 When containing one or more substituents, the substituents are each independently selected from deuterium, halogen, cyano, C1-C6 (such as C2, C3, C4, C5, etc.) straight or branched alkyl, C3-C6 (such as C4, C5, etc.) cycloalkyl, C6-C10 (such as C6, C9, C10) aryl, C3-C10 (such as C3, C4, C5, C6, C9, C10) heteroaryl, or any combination of at least two of them. In some embodiments, when R U2 When containing one or more substituents, the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl or phenyl. In some embodiments, when R U2 When containing two or more substituents, any two adjacent substituents are not connected or are connected by a chemical bond to form a 5-6 membered ring.

[0059] In some embodiments, R U2 Is selected from hydrogen, deuterium, fluorine, cyano, or any one of the following groups:

[0060]

[0061] In some embodiments, X is selected from CR x1 R x2 , NR x3 , SiR x4 R x5 , S, O or Se; the Rx1 , R x2 , R x3 , R x4 , R x5 Each independently selected from hydrogen, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, and any one of the R x1 , R x2 or R x4 , R x5 are not connected or connected by a chemical bond to form a ring; wherein when one or more substituents are included in the R x1 , R x2 , R x3 , R x4 , R x5 , each of the substituents is independently selected from deuterium, halogen, cyano, C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or any one or at least two combinations thereof.

[0062] In some embodiments, the R x1 , R x2 , R x3 , R x4 , R x5 Each independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl or pyridyl.

[0063] In some embodiments, X is selected from S, O or Se; in some embodiments, X is selected from S or O.

[0064] In some embodiments, the first ligand L a has a structure shown in any one of formulas (II-1) - (II-6):

[0065]

[0066] Among them, R 1 and R 2 , n, and X are defined in the same way as in formula (I); R Za -R Zd is defined in the same way as R Z in formula (I), R U1a -R U1d is defined in the same way as R U1 in formula (I), R U2a -R U2d is defined in the same way as R U2 in formula (I).

[0067] In some embodiments, in formulas (II-1)-(II-6), the R Za -R Zd , R U1a -R U1d , and R U2a -R U2d are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, hydroxy, ester, amino, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, and substituted or unsubstituted C3-C30 heteroaryloxy; any two adjacent groups between R Za -R Zd are not connected or are connected by a chemical bond to form a ring; any two adjacent groups between R U1a -R U1d are not connected or are connected by a chemical bond to form a ring; any two adjacent groups between R U2a -R U2d are not connected or are connected by a chemical bond to form a ring.

[0068] In some embodiments, in formulas (II-1)-(II-6), n is selected from any integer from 1 to 6 (such as 2, 3, 4, 5, etc.). In some embodiments, in formulas (II-1)-(II-6), n is selected from 1, 2, or 3.

[0069] In some embodiments, in formulas (II-1)-(II-6), R 1 and R 2Independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl groups, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl groups, substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, substituted or unsubstituted C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl groups, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl groups, and substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl groups.

[0070] In some embodiments, in formulas (II-1)-(II-6), R 1 , R 2 are independently selected from any one of hydrogen, deuterium, C1-C6 straight-chain or branched-chain alkyl groups, and deuterated C1-C6 straight-chain or branched-chain alkyl groups.

[0071] In some embodiments, in formulas (II-1)-(II-6), R 1 , R 2 are independently selected from any one of hydrogen, deuterium, or the following groups:

[0072]

[0073] In some embodiments, in formulas (II-1)-(II-6), the R Za -R Zd , R U1a -R U1d , R U2a -R U2dIndependently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (such as C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryloxy.

[0074] In some embodiments, in formulas (II-1)-(II-6), R Za -R Zd Independently selected from any one of hydrogen, deuterium, C1-C6 linear or branched alkyl, deuterated C1-C6 linear or branched alkyl.

[0075] In some embodiments, in formulas (II-1)-(II-6), R Za -R ZdIndependently selected from any one of hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, propyl, deuterated propyl, isopropyl, deuterated isopropyl, butyl, deuterated butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, n-pentyl, neopentyl, isopentyl, deuterated n-pentyl, deuterated neopentyl, deuterated isopentyl.

[0076] In some embodiments, in formula (II-1)-formula (II-6), R Za -R Zd Any 2-4 of them are hydrogen. In some embodiments, in formula (II-1)-formula (II-6), R Za -R Zd Any 3-4 of them are hydrogen. In some embodiments, in formula (II-1)-formula (II-6), R Za -R Zd All are hydrogen.

[0077] In some embodiments, in formula (II-1)-formula (II-6), R U1a -R U1d Independently selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 straight-chain or branched-chain alkyl, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl.

[0078] In some embodiments, in formula (II-1)-formula (II-6), R U1a -R U1d Independently selected from any one of hydrogen, deuterium, fluorine, cyano, C1-C6 straight-chain or branched-chain alkyl, deuterated C1-C6 straight-chain or branched-chain alkyl, phenyl, deuterated phenyl.

[0079] In some embodiments, in formula (II-1)-formula (II-6), R U1a -R U1d Independently selected from any one of hydrogen, deuterium, fluorine, cyano, or any of the following groups:

[0080]

[0081] In some embodiments, in formula (II-1)-formula (II-6), R U2a -R U2d Any 2-4 of them are hydrogen. In some embodiments, in formula (II-1)-formula (II-6), R U2a -R U2d Any 2-3 of them are hydrogen. In some embodiments, in formula (II-1)-formula (II-6), R U2a -R U2dAny 3 to 4 of them are hydrogen. In some embodiments, in Formula (II-1) - Formula (II-6), R U2a -R U2d Any 3 of them are hydrogen. In some embodiments, in Formula (II-1) - Formula (II-6), R U2a -R U2d All are hydrogen.

[0082] In some embodiments, in Formula (II-1) - Formula (II-6), X is selected from CRx 1 Rx 2 , NRx 3 , SiRx 4 Rx 5 , S, O or Se, any one of them.

[0083] In some embodiments, in Formula (II-1) - Formula (II-6), the Rx 1 , Rx 2 , Rx 3 , Rx 4 , Rx 5 Each independently is selected from hydrogen, substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched-chain alkyl, substituted or unsubstituted C6-C30 (such as C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, any one of them, and the Rx 1 , Rx 2 or Rx 4 , Rx 5 are not connected or are connected by a chemical bond to form a ring.

[0084] In some embodiments, in Formula (II-1) - Formula (II-6), X is selected from S, O or Se. In some embodiments, in Formula (II-1) - Formula (II-6), X is selected from S or O.

[0085] In some embodiments, the first ligand L a has the structure shown in any one of Formula (II-1-1) to (II-1-3), Formula (II-2-1) to (II-2-3), Formula (II-3-1) to (II-3-3), Formula (II-4-1) to (II-4-3), Formula (II-5-1) to (II-5-3), Formula (II-6-1) to (II-6-3):

[0086]

[0087]

[0088]

[0089] Among them, the definition of X is the same as that in formula (I); R Za -R Zd 、R U1a -R U1d 、R U2a -R U2d are defined in the same way as in formulas (II-1)-(II-6); R 1a 、R 1b 、R 1c are defined in the same way as R 1 in formulas (II-1)-(II-6), and R 2a 、R 2b 、R 2c are defined in the same way as R 2 in formulas (II-1)-(II-6).

[0090] In some embodiments, R 1a 、R 1b 、R 1c 、R 2a 、R 2b 、R 2c are all hydrogen.

[0091] In some embodiments, 1-4 of R 1a 、R 1b 、R 1c 、R 2a 、R 2b 、R 2c are independently selected from any one of deuterium, C1-C6 straight-chain or branched-chain alkyl, and deuterated C1-C6 straight-chain or branched-chain alkyl, and the others are hydrogen.

[0092] In some embodiments, 1-4 of R 1a 、R 1b 、R 1c 、R 2a 、R 2b 、R 2c are independently selected from hydrogen, deuterium, or any one of the following groups:

[0093]

[0094] and the others are hydrogen.

[0095] According to some embodiments of the present invention, the first ligand L aIt has the structure shown below, where X is selected from S, O or Se:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] According to some embodiments of the present invention, the metal complex further comprises a second ligand L coordinated to the metal atom M b and / or a third ligand L c , and the structural formula of the metal complex is M(L a ) i (L b ) j (L c ) k ; wherein, i is selected from 1 or 2, j is selected from 0, 1 or 2, k is selected from 0 or 1; the sum of i, j, and k is equal to the oxidation state of M;

[0104] The second ligand L b and the third ligand L c are each independently selected from the structures shown in formula (III) and formula (IV):

[0105]

[0106] Wherein, R 3 ~R 10 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched-chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-20 alkoxy, substituted or unsubstituted C1-20 alkylsilyl, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C3-30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, and no two adjacent groups among R 3 ~R 10 are connected or connected by a chemical bond to form a ring;

[0107] R 31 ~R 37 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-20 alkoxy, substituted or unsubstituted C1-20 alkylsilyl, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C3-30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, and any one of them, the R 31 ~R 37 there is no connection or they are connected by a chemical bond to form a ring between two adjacent groups among them;

[0108] the R 3 ~R 10 、R 31 ~R 37 when containing one or more substituents, the substituents are each independently selected from deuterium, halogen, cyano, nitro, hydroxy, amino, C1-C20 straight-chain or branched alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, C3-C30 heteroaryl, and any one or a combination of at least two of them.

[0109] In some embodiments, when i is 2, the two Ls a can be the same or different; when j is 2, the two Ls b can be the same or different.

[0110] In some embodiments, R 3 ~R 10 are each independently selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 straight-chain or branched alkyl, substituted or unsubstituted C1-C6 alkylsilyl, substituted or unsubstituted C6-C12 aryl.

[0111] In some embodiments, R 3 ~R 10 are each independently selected from hydrogen, deuterium, fluorine, cyano, trifluoromethyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated isobutyl, deuterated tert-butyl, trimethylsilyl, triethylsilyl, phenyl, deuterated phenyl.

[0112] In some embodiments, R 31 ~R37 Each independently selected from any one of hydrogen, deuterium, fluorine, cyano group, substituted or unsubstituted C1-C6 straight-chain or branched-chain alkyl group, and substituted or unsubstituted C3-C8 cycloalkyl group.

[0113] In some embodiments, R 31 ~R 37 Each independently selected from any one of hydrogen, deuterium, fluorine, cyano group, trifluoromethyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, 3-methylpentyl group, 2,4-dimethylpentyl group, 2,2,4,4-tetramethylpentyl group, deuterated methyl group, deuterated ethyl group, deuterated propyl group, deuterated isopropyl group, deuterated butyl group, deuterated isobutyl group, deuterated tert-butyl group, cyclopentyl group, cyclohexyl group, cyclopentyl group substituted by one or more substituents selected from deuterium, fluorine, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, and cyclohexyl group substituted by one or more substituents selected from deuterium, fluorine, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group.

[0114] According to some embodiments of the present invention, the L a , L b and L c can optionally be connected to form a multidentate ligand; for example, any two of L a , L b and L c can be connected to form a tetradentate ligand; and for another example, L a , L b and L c can be connected to each other to form a hexadentate ligand.

[0115] According to some embodiments of the present invention, the L b , L c each independently selected from any one of the following structures:

[0116]

[0117]

[0118] Wherein, the dashed line represents the binding site of the ligand to the metal atom M.

[0119] According to some embodiments of the present invention, the metal atom M is selected from transition metals or noble metals. According to some embodiments of the present invention, the metal atom M is selected from Cu, Pt, Au, Ru, Pd, Rh or Ir. In a preferred embodiment, the metal atom M is selected from Pt or Ir. According to the preferred embodiment of the present invention, the metal atom M is selected from Ir.

[0120] As a preferred embodiment of the present invention, the metal-organic complex is arbitrarily selected from the following compounds 1-160: wherein the compounds 1 to 120 have Ir(L a ) 2 (L b ) or Ir(L a ) 2 (L c ) structures, where the two L a are the same, and L a , L b or L c are respectively selected from the structures listed in Table 1 below:

[0121] Table 1

[0122]

[0123]

[0124]

[0125] The compounds 121 to 160 have the structure of Ir(L a )(L b ) 2 , where the two L b are the same, and L a and L b are respectively selected from the structures listed in Table 2 below:

[0126] Table 2

[0127]

[0128] In a second aspect, the present invention provides the application of the metal-organic complex described in the first aspect in an organic electronic device.

[0129] Specifically, the organic electronic device includes but is not limited to: an organic light-emitting device, an optical sensor, a solar cell, a lighting element, an organic thin-film transistor, an organic field-effect transistor, an organic thin-film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or an electronic paper. The metal-organic complex of the present invention is most preferably applicable to an organic light-emitting device.

[0130] In some embodiments, the metal-organic complex is used as a dye material for a host material in an organic light-emitting device. The metal-organic complex of the present invention is used as a doped dye in an organic light-emitting device to emit light, and the electroluminescent device prepared using the metal-organic complex of the present invention exhibits excellent properties of high purity, high brightness, and high efficiency.

[0131] In a third aspect, the present invention provides an organic electroluminescent device, which includes a light-emitting layer, and the light-emitting layer includes the metal-organic complex provided in the first aspect of the present invention.

[0132] As a light-emitting dye in the light-emitting layer of the organic electroluminescent device, the metal-organic complex of the present invention enables such organic electroluminescent devices to exhibit superior properties of high purity, high brightness, and high efficiency.

[0133] Furthermore, the organic electroluminescent device provided by the present invention includes a substrate, and an anode layer, a plurality of light-emitting unit layers, and a cathode layer formed on the substrate in sequence; the light-emitting unit layer includes a light-emitting layer.

[0134] Furthermore, the organic electroluminescent device further includes one or more of a hole injection layer, a hole transport layer, an electron transport layer, an electron blocking layer, etc. The hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and there are multiple light-emitting layers between the hole transport layer and the electron transport layer. Preferably, the light-emitting dye in the light-emitting layer is the light-emitting material of the present invention.

[0135] Further preferably, the doping concentration of the metal-organic complex of the present invention in the host material is 1-12%, such as 1%, 2%, 3%, 5%, 6%, 7%, 8%, 10%, 12% or any value between them, more preferably 1-8%, and even more preferably 2-7%. When the doping concentration of the metal-organic complex in the host material is about 2%, the performance of the device is the best. The doping concentration is the mass percentage concentration.

[0136] In a fourth aspect, the present invention provides a display device, which includes the organic electroluminescent device.

[0137] In a fifth aspect, the present invention provides a lighting device, which includes the organic electroluminescent device.

[0138] Compared with the prior art, the present invention has the following beneficial effects:

[0139] The present invention provides a class of metal-organic complexes, which can be used as phosphorescent light-emitting materials, effectively solving the problems existing in currently commonly used phosphorescent materials in terms of color purity, luminescence efficiency, and lifespan. The organic electroluminescent devices prepared using the metal-organic complexes of the present invention exhibit superior properties of high purity, high brightness, and high efficiency. Detailed embodiments

[0140] The technical solutions of the present invention will be described in detail below through specific embodiments. The following embodiments are used to illustrate the present invention, but are not used to limit the scope of the present invention. Any equivalent changes or modifications made without departing from the spirit disclosed by the present invention shall be included within the scope of the claims.

[0141] Definition

[0142] Unless otherwise defined, all technical and scientific terms used in the present invention have the same meaning as commonly used in the field to which the present invention pertains. For the purpose of explaining this specification, the following definitions will be applied, and where appropriate, terms used in the singular form will also include the plural form, and vice versa.

[0143] In the present invention, the group of "substituted or unsubstituted" may be substituted with one substituent or multiple substituents. When there are multiple substituents (at least two), they may be the same or different substituents; when the same expression is involved herein, it has the same meaning. Unless otherwise specified, the selection range of the substituted substituents is as shown above and will not be elaborated further.

[0144] It should be noted that in the present invention, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the essential reason for obtaining good performance is the optimized combination of the entire molecular structure, which is the result of the synergistic effect between each group, rather than the effect of a single group / feature.

[0145] The above is the preferred technical solution of the present invention, but it does not limit the technical solution provided by the present invention. Through the above preferred technical solution, the purpose and beneficial effects of the present invention can be better achieved and realized.

[0146] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. When the same description is involved herein, it has the same meaning.

[0147] In the present invention, for the expression of chemical elements, unless otherwise specified, it includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0148] In the present invention, unless otherwise specified, the heteroatoms of heteroaryl are selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatoms in heterocycloalkyl are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0149] In the present invention, the expression of the ring structure crossed by "-" indicates that the connection site is at any bond-forming position on the ring structure.

[0150] In the present invention, "*" all represent the connection sites of the groups.

[0151] In the present invention, "independently of each other" means that when the subject has a plurality of them, they can be the same or different from each other.

[0152] In the present invention, the expression of Ca-Cb represents that the group has a carbon atom number of a-b. Without special instructions, the carbon atom number does not include the carbon atom number of the substituents.

[0153] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0154] The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0155] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0156] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0157] In the present invention, unless otherwise specified, the C6-C30 aryl group (C6-C30 aromatic ring) includes monocyclic aryl groups and polycyclic aryl groups; the monocyclic aryl group means that the group contains at least 1 phenyl group. When there are at least 2 phenyl groups, the phenyl groups are connected by single bonds. Exemplarily, it includes but is not limited to: phenyl group, biphenyl group, terphenyl group, quaterphenyl group, etc.; the polycyclic aryl group means that the group contains at least 2 rings (and at least 1 ring is an aromatic ring), and the rings are fused to each other by sharing two adjacent carbon atoms. Exemplarily, it includes but is not limited to: naphthyl group, anthracenyl group, phenanthryl group, indenyl group, fluorenyl group and its derivatives (9,9-dimethylfluorenyl group, 9,9-diethylfluorenyl group, 9,9-dipropylfluorenyl group, 9,9-dibutylfluorenyl group, 9,9-dipentylfluorenyl group, 9,9-dihexylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-dinaphthylfluorenyl group, spirobifluorenyl group, benzofluorenyl group, etc.), fluoranthenyl group, triphenylenyl group, pyrenyl group, perylenyl group, Groups such as a base, a tetraphenyl group, an acenaphthylenyl group, a benzacenaphthylenyl group, etc. It should be noted that a monocyclic aryl group and a polycyclic aryl group connected by a single bond also belong to the scope of aryl groups. For example, phenylnaphthyl, naphthylphenyl, binaphthyl, etc.

[0158] The C6-C30 heteroaryl group (C3-C30 heteroaromatic ring) includes a monocyclic heteroaryl group or a polycyclic heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as an aryl group, a heteroaryl group, etc.), the heteroaryl group and other groups are connected by a single bond. Exemplarily, it includes but is not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The polycyclic heteroaryl group means that the molecule contains at least one heteroaromatic ring and an aromatic ring (heteroaromatic ring or aryl ring), and the two are fused to each other by sharing two adjacent atoms. Exemplarily, it includes but is not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl groups connected by a single bond and heteroaryl groups, and aryl groups and heteroaryl groups connected by a single bond also belong to the scope of heteroaryl groups. For example, phenylpyridyl, pyridylphenyl, phenylpyrimidinyl, diphenylpyridyl, etc.

[0159] Specific examples of the C6-C30 arylamino group are monovalent groups in which at least one hydrogen in -NH 2 is replaced by the above-mentioned aryl group. Exemplarily, it includes but is not limited to: phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, etc. Specific examples of the C3-C30 heteroarylamino group are monovalent groups in which at least one hydrogen in -NH 2 is replaced by the above-mentioned heteroaryl group. Exemplarily, it includes but is not limited to: pyridylamino, pyrimidinylamino, dibenzofurylamino, etc.

[0160] The C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl group with O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl group with O.

[0161] The C1-C20 linear or branched alkyl group, preferably a C1-C16 linear or branched alkyl group, more preferably a C1-C10 linear or branched alkyl group, exemplarily includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0162] Specific examples of the C1-C20 alkoxy group can be a monovalent group obtained by connecting an O to the examples of the above-mentioned linear or branched alkyl groups.

[0163] Specific examples of the C1-C20 alkylsilyl group are monovalent groups in which at least one hydrogen in -SiH 3 is replaced by the above-mentioned linear or branched alkyl group, exemplarily including but not limited to: trimethylsilyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, triethylsilyl, tripropylsilyl, etc.

[0164] The C3-C20 cycloalkyl group, preferably a C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. Among them, the monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and the polycyclic alkyl group refers to a structure formed by two or more cycloalkyl groups sharing one or more ring carbon atoms; exemplarily includes but is not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0165] Specific examples of the C2-C20 heterocycloalkyl group can be groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), exemplarily including but not limited to: epoxy group, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxanyl, morpholinyl, etc.

[0166] The synthesis route of the metal-organic complex of the present invention is as follows. Those skilled in the art should understand that similar routes can also be used for the synthesis of other routes.

[0167] Preparation Example 1: Synthesis of Ligand H1

[0168]

[0169] The synthesis route is as follows:

[0170]

[0171] (1) Synthesis of Intermediate H1-1:

[0172] Under nitrogen protection, 1-acetonaphthone (35 g) and tetrahydrofuran (350 mL) were added to a dry 500 mL three-necked reaction flask. The temperature of the system was cooled to -10 °C, and tert-butylmagnesium chloride (206 mL) was added dropwise while maintaining this temperature. The addition was completed within 0.5 h, and the reaction was carried out at room temperature for 12 h. A saturated ammonium chloride solution (100 mL) and ethyl acetate (200 mL) were added to the reaction system, stirred, allowed to stand and separated. After the organic phase was concentrated under reduced pressure to remove the solvent, dichloromethane (100 mL) and silica gel (70 g) were added to prepare a dry sample, which was purified by column chromatography. The eluent was distilled under reduced pressure to obtain intermediate H1-1 (19.7 g, yield 44%).

[0173] (2) Synthesis of intermediate H1-2:

[0174] Under nitrogen protection, intermediate H1-1 (19.7 g) and dichloromethane (200 mL) were added to a dry 500 mL three-necked reaction flask. A prepared 50% mass fraction aluminum trichloride-nitromethane solution (18.46 g) was added dropwise at ambient temperature. After reacting for 2 h, the reaction system was slowly added to an aqueous hydrochloric acid solution (32 mL), allowed to stand and separated. The organic phase was washed with water until neutral, concentrated under reduced pressure to remove the solvent to obtain an oily substance. n-Heptane (60 mL) was added to dissolve the oily substance for column chromatography. The eluent was distilled under reduced pressure, ethanol (20 mL) was added, and the mixture was crystallized by freezing. Filtration was carried out at 0 °C to obtain intermediate H1-2 (12.93 g, yield 71.29%).

[0175] (3) Synthesis of intermediate H1-3:

[0176] Under nitrogen protection, intermediate H1-2 (12.93 g) and DMF (130 mL) were added to a dry 500 mL three-necked reaction flask. After heating to 40 °C, an NBS solution (11.51 g) was added dropwise, and the reaction was carried out with heat preservation for 4 h. After cooling to room temperature, deionized water (750 mL) was added, and a yellow solid was obtained by filtration. Ethanol (20 ml) was added and the mixture was slurried at room temperature and filtered. Ethanol (60 mL) was added, heated to reflux until clear, cooled to 10 °C and filtered to obtain intermediate H1-3 (13.48 g, yield 75.78%).

[0177] (4) Synthesis of intermediate H1-4:

[0178] Under nitrogen protection, intermediate H1-3 (13.48 g), bis(pinacolato)diboron (14.19 g), anhydrous potassium acetate (9.14 g), tris(dibenzylideneacetone)dipalladium(0) (0.21 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.22 g) and toluene (100 mL) were successively added to a dry 1 L three-necked reaction flask. Heating was started, and the temperature was raised to 105 °C for reflux. The reaction was maintained at this temperature for 12 h. After cooling to room temperature, toluene (200 mL) and water (200 mL) were added to the reaction system. After standing and separating the liquid, the organic phase was subjected to column chromatography. When the eluent was concentrated to 15 mL of toluene remaining, n-heptane (30 mL) was added for reflux pulping and suction filtration. After drying, intermediate H1-4 (13.41 g, yield 86%) was obtained.

[0179] (5) Synthesis of intermediate H1-5:

[0180] Under nitrogen protection, intermediate H1-4 (13.41 g), 1,7-dichloro-8-methylbenzo[4,5]thieno[2,3-c]pyridine (10.69 g), anhydrous potassium carbonate (11.01 g), tetrakis(triphenylphosphine)palladium(0) (2.3 g), dioxane (50 mL) and deionized water (10 mL) were successively added to a dry 250 mL three-necked reaction flask. The mixture was heated and stirred, and the reaction was maintained at 85 °C - 90 °C for 8 h. After cooling to room temperature, deionized water (100 mL) was added, stirred for 15 min and suction filtered. Toluene (100 mL) was added for reflux and water separation. The temperature was lowered to 80 °C - 85 °C for column chromatography. The eluent was concentrated to remove the solvent, ethyl acetate (30 mL) and n-heptane (15 mL) were added for reflux pulping, and suction filtration was carried out at room temperature. After drying, intermediate H1-5 (14.35 g, yield 81.33%) was obtained.

[0181] (6) Synthesis of ligand H1:

[0182] Under nitrogen protection, intermediate H1-5 (14.35 g), neopentylboronic acid (18.83 g), anhydrous potassium phosphate (20.65 g), potassium fluoride (37.66 g), tris(dibenzylideneacetone)dipalladium(0) (1.49 g), tricyclohexylphosphine tetrafluoroborate (1.2 g) and toluene (225 mL) were successively added to a dry 500 mL three-necked reaction flask. The mixture was heated and stirred, and the reaction was maintained at 105 °C for 2 h. After cooling to room temperature, the reaction solution was suction filtered to remove inorganic salts. The organic phase was washed with water until neutral and then subjected to column chromatography. The eluent was concentrated to remove the solvent, ethanol (45 mL) was added for reflux pulping, and suction filtration was carried out at room temperature. Toluene (90 mL) was added for recrystallization, and suction filtration was carried out at room temperature. The mixture was repeatedly pulped with ethyl acetate and heptane, and suction filtration was carried out at room temperature. After drying, ligand H1 (10.23 g, yield 64.52%) was obtained.

[0183] MS (m / e) of ligand H1: 477.18. For ligand H1 1HNMR (400 MHz, CDCl 3 , ppm): δ

[0184] 8.60 (d, 1H), 8.14 - 8.08 (m, 1H), 7.89 - 7.80 (m, 2H), 7.72 (d, 1H), 7.46 - 7.39 (m, 3H), 7.11 (d, 1H), 2.65 (s, 2H), 2.44 (s, 3H), 1.39 (s, 12H), 0.89 (s, 9H).

[0185] Preparation Example 2: Synthesis of Ligand H2:

[0186]

[0187] The synthesis route is as follows:

[0188]

[0189] (1) Synthesis of Intermediate H2-1:

[0190] Under nitrogen protection, add naphthalene (12.8 g) and dichloroethane (200 mL) to a dry 500 mL three-necked reaction flask in sequence, stir and cool down to 0 °C to -10 °C, add anhydrous aluminum trichloride (17.35 g), control the temperature at 0 °C to -10 °C and dropwise add a solution composed of methyl 3-bromo-3-methylbutyrate (19.5 g) and dichloroethane (20 mL). After dropping, keep the temperature for 0.5 h, naturally warm up to room temperature, stir for 2 h, monitor by TLC. When the raw material naphthalene has reacted completely, pour the reaction solution into ice water (500 mL), let it stand for liquid separation, wash the organic phase to neutral, add anhydrous sodium sulfate for drying, filter, evaporate the solvent in the filtrate under vacuum, dissolve the residue in ethanol (50 mL) for crystallization, and filter to obtain Intermediate H2-1 (21.3 g, yield 88%).

[0191] (2) Synthesis of Intermediate H2-2:

[0192] Under nitrogen protection, add tetrahydrofuran (600 mL) and Intermediate H2-1 (121 g) to a dry 2 L three-necked reaction flask, stir and cool down to -10 °C to -5 °C under nitrogen protection, dropwise add a tetrahydrofuran solution of methylmagnesium chloride (500 mL), which takes about 1 h, keep the temperature at 0 °C to -5 °C for 1 h, naturally warm up to room temperature and stir for 8 h, dropwise add concentrated hydrochloric acid (100 mL) below 0 °C, stir for 5 min, add ethyl acetate (500 mL), let it stand for liquid separation, wash the organic phase to neutral, evaporate the solvent completely under vacuum to obtain Intermediate H2-2 (121 g, yield 100%).

[0193] (3) Synthesis of Intermediate H2-3:

[0194] Add intermediate H2-2 (121 g), glacial acetic acid (400 mL) and concentrated hydrochloric acid (32 mL) to a dry 1000 mL three-necked reaction flask. Stir and heat up to 100 °C for reaction for 4 h. Monitor by TLC. After the raw materials are completely reacted, cool down to room temperature, pour into ice water, extract with dichloromethane (300 mL). Wash the organic phase to neutral, evaporate the solvent at atmospheric pressure. Dissolve the residue with absolute ethanol (40 mL) and toluene (20 mL) for crystallization, filter and dry to obtain intermediate H2-3 (56 g, yield 50%).

[0195] (4) Synthesis of intermediate H2-4:

[0196] Similar to the synthesis process of intermediate H1-3, replace intermediate H1-2 with intermediate H2-3, and prepare intermediate H2-4 (53.41 g, yield 70.8%) according to the method in Preparation Example of intermediate H1-3.

[0197] (5) Synthesis of intermediate H2-5:

[0198] Similar to the synthesis process of intermediate H1-4, replace intermediate H1-3 with intermediate H2-4, and prepare intermediate H2-5 (50.84 g, yield 82.1%) according to the method in Preparation Example of intermediate H1-4.

[0199] (6) Synthesis of intermediate A-1:

[0200] Add water (200 mL) and dioxane (400 mL) to a dry 1 L three-necked reaction flask. Stir in sodium hydroxide (4.8 g), 4-iodo-3-amino-2-chloropyridine (25.45 g) and o-chlorothiophenol (14.45 g). Heat up to 50 to 60 °C and stir for 7 h. Monitor by TLC. After the raw materials are completely reacted, add toluene (300 mL). Let it stand and separate the liquid. Wash the organic phase to neutral, evaporate the solvent under vacuum. Dissolve the residue with toluene (300 mL) and pass through a column. Concentrate the eluate at atmospheric pressure to about 60 mL, cool down to 25 °C, filter and dry to obtain intermediate A-1 (22.49 g, yield 83%).

[0201] (7) Synthesis of intermediate A:

[0202] Under nitrogen protection, tetrahydrofuran (90 mL) and glacial acetic acid (280 mL) were added to a dry 1 L three-necked reaction flask. Intermediate A-1 (22.49 g) was added with stirring, and the temperature was lowered to -10 °C to -5 °C. tert-Butyl nitrite (12.82 g) was added dropwise over about 0.5 h. After the addition was complete, the mixture was stirred at room temperature with natural temperature rise for 3 h. Monitored by TLC, the raw materials reacted completely. Dichloromethane (300 mL) was added, and the mixture was allowed to stand and separated. The organic phase was washed to neutral, and the solvent was evaporated under vacuum. The residue was dissolved in toluene (300 mL) and passed through a column. The eluent was concentrated under normal pressure to about 60 mL, the temperature was lowered to 25 °C, filtered, and dried to obtain Intermediate A (12.86 g, yield 61%).

[0203] (8) Synthesis of Intermediate H2-6:

[0204] Similar to the synthesis process of Intermediate H1-5, Intermediate H1-4 and 1,7-dichloro-8-methylbenzo[4,5]thieno[2,3-c]pyridine were replaced with Intermediate H2-5 and Intermediate A, and Intermediate H2-6 (18.88 g, yield 84.2%) was prepared according to the method in Preparation Example of Intermediate H1-5.

[0205] (9) Synthesis of Ligand H2:

[0206] Similar to the synthesis process of Ligand H1, Intermediate H1-5 and neopentylboronic acid were replaced with Intermediate H2-6 and 4-tert-butylphenylboronic acid, and Ligand H2 (13.29 g, yield 57.6%) was prepared according to the method in Preparation Example of Ligand H1.

[0207] MS (m / e) of Ligand H2: 539.59. 1 HNMR (400 MHz, CDCl 3 , ppm): δ

[0208] 8.56 (d, 1H), 8.15 - 8.07 (m, 2H), 7.96 - 7.84 (m, 3H), 7.60 - 7.53 (m, 3H), 7.46 - 7.28 (m, 5H), 2.16 (d, 1H), 2.00 (d, 1H), 1.38 - 1.32 (t, 21H).

[0209] Preparation Example 3: Synthesis of Ligand H3:

[0210]

[0211] The synthesis route is as follows:

[0212]

[0213] (1) Synthesis of Intermediate B-1:

[0214] Similar to the synthesis process of intermediate A-1, 4-iodo-3-amino-2-chloropyridine was replaced with 3-amino-4-iodo-6-chloropyridine, and intermediate B-1 (23.32 g, yield 86.4%) was prepared according to the method in Preparation Example of intermediate A-1.

[0215] (2) Synthesis of intermediate B:

[0216] Similar to the synthesis process of intermediate A, intermediate A-1 was replaced with intermediate B-1, and intermediate B (13.48 g, yield 61.7%) was prepared according to the method in Preparation Example of intermediate A.

[0217] (3) Synthesis of intermediate H3-1:

[0218] Similar to the synthesis process of intermediate H1-5, 1,7-dichloro-8-methylbenzo[4,5]thieno[2,3-c]pyridine was replaced with intermediate B, and intermediate H3-1 (12.87 g, yield 72.8%) was prepared according to the method in Preparation Example of intermediate H1-5.

[0219] (4) Synthesis of ligand H3:

[0220] Similar to the synthesis process of ligand H1, intermediate H1-5 and pivalylboronic acid were replaced with intermediate H3-1 and phenylboronic acid, and ligand H3 (7.55 g, yield 55.4%) was prepared according to the method in Preparation Example of ligand H1.

[0221] MS (m / e) of ligand H3: 469.65. 1 HNMR (400 MHz, CDCl 3 , ppm): δ

[0222] 8.83 (s, 1H), 8.21 - 8.09 (m, 2H), 7.89 (dd, 1H), 7.79 - 7.68 (t, 2H), 7.64 - 7.34 (m, 9H), 1.40 (s, 12H).

[0223] Preparation Example 4: Synthesis of ligand H4:

[0224]

[0225] The synthesis route is as follows:

[0226]

[0227] (1) Synthesis of intermediate H4-1:

[0228] Add 4-bromo-1-naphthoic acid (125.5 g), thionyl chloride (214 g) and DMF (1 g) to a dry 1000 mL three-necked reaction flask, stir and heat up to 75 °C for heat preservation for 8 h, cool down to room temperature, and distill off the excessive thionyl chloride under vacuum to obtain intermediate H4-1 (132 g, yield 98%).

[0229] (2) Synthesis of intermediate H4-2:

[0230] Under nitrogen protection, add xylene (200 mL) to a dry 1000 mL three-necked reaction flask, add intermediate H4-1 (132 g), anhydrous potassium carbonate (135 g), pivalic acid (75 g), tricyclohexylphosphine (5.8 g), and tris(dibenzylideneacetone)dipalladium(0) (6 g) under stirring, heat up to 140 °C for reflux reaction for 24 h, monitor by TLC, when the raw materials react completely, cool down to room temperature, add water (100 mL) as a supplement, separate the liquid, wash the organic phase with water until neutral, distill off the solvent under vacuum, dissolve the residue with toluene (300 mL) and carry out column chromatography, concentrate the eluent under normal pressure to about 60 mL, cool down to 25 °C, filter, and dry to obtain intermediate H4-2 (53.6 g, yield 47%).

[0231] (3) Synthesis of intermediate H4-3:

[0232] Add monoethylene glycol (200 mL), potassium hydroxide (16 g), hydrazine hydrate (23 g) and intermediate H4-2 (53.6 g) to a dry 500 mL three-necked reaction flask, stir and heat up to 160 °C to 170 °C for reaction for 8 h, monitor by TLC, when the raw materials react completely, cool down to room temperature, add water (20 mL) and toluene (100 mL) as supplements, let it stand and separate the liquid, wash the organic phase until neutral, distill off the solvent under vacuum, dissolve the residue with toluene (30 mL) for crystallization, filter and dry to obtain intermediate H4-3 (40.3 g, yield 80%).

[0233] (4) Synthesis of intermediate H4-4:

[0234] Similar to the synthesis process of intermediate H1-4, replace intermediate H1-3 with intermediate H4-3, and prepare intermediate H4-4 (39.02 g, yield 79.3%) according to the method in Preparation Example of intermediate H1-4.

[0235] (5) Synthesis of intermediate C-1:

[0236] Under nitrogen protection, to a dry 1000 mL three-necked reaction flask, add toluene (250 mL), absolute ethanol (125 mL), water (125 mL) and anhydrous potassium carbonate (51.75 g). While stirring, add o-methoxyphenylboronic acid (38 g), 3-amino-4-iodo-2-chloropyridine (63.63 g), and tetrakis(triphenylphosphine)palladium(0) (2 g). Heat the mixture to 73 °C and react for 18 h. Monitor the reaction by TLC. After the raw materials are completely reacted, cool the reaction mixture to room temperature, add water (100 mL), separate the layers, wash the organic phase with water until neutral, evaporate the solvent under vacuum, dissolve the residue in toluene (300 mL) and pass it through a column. Concentrate the eluent under normal pressure to about 60 mL, cool it to 25 °C, filter, and dry to obtain intermediate C-1 (38.1 g, yield 65%).

[0237] (6) Synthesis of intermediate C:

[0238] Under nitrogen protection, to a dry 1000 mL three-necked reaction flask, add tetrahydrofuran (100 mL) and glacial acetic acid (300 mL). While stirring, add C-1 (38.1 g). Cool the mixture to -10 °C to -5 °C, and dropwise add tert-butyl nitrite (25 g) over about 0.5 h. After the addition is complete, stir at room temperature for 3 h while allowing the temperature to rise naturally. Monitor the reaction by TLC. After the raw materials are completely reacted, add dichloromethane (300 mL), let it stand and separate the layers, wash the organic phase until neutral, evaporate the solvent completely under vacuum, dissolve the residue in toluene (300 mL) and pass it through a column. Concentrate the eluent under normal pressure to about 60 mL, cool it to 25 °C, filter, and dry to obtain intermediate C (19.74 g, yield 60%).

[0239] (7) Synthesis of ligand H4:

[0240] Similar to the synthesis process of intermediate H1-5, replace intermediate H1-4 and 1,7-dichloro-8-methylbenzo[4,5]thieno[2,3-c]pyridine with intermediate H4-4 and intermediate C, and prepare ligand H4 (15.85 g, yield 53.1%) according to the method in Preparation Example of intermediate H1-5.

[0241] MS (m / e) of ligand H4: 307.15. 1 HNMR (400 MHz, CDCl 3 , ppm): δ

[0242] 8.75 (s, 1H), 8.14 - 7.98 (m, 3H), 7.87 (s, 1H), 7.66 - 7.32 (m, 6H), 4.13 - 4.00 (dd, 2H).

[0243] Preparation Example 5: Synthesis of ligand H5:

[0244]

[0245] The synthesis route is as follows:

[0246]

[0247] (1) Synthesis of intermediate H5-1:

[0248] Under nitrogen protection, add tetrahydrofuran (300 mL) and methyl 1-naphthoate (93 g) to a dry 1 L three-necked reaction flask. Stir and cool down to -10°C to -5°C, then dropwise add a tetrahydrofuran solution of methylmagnesium chloride (250 mL) over about 1 h. Keep the temperature at 0°C to -5°C for 1 h, then stir at room temperature for 8 h. Dropwise add concentrated hydrochloric acid (80 mL) below 0°C, stir for 5 min, add ethyl acetate (400 mL), let it stand for liquid separation. Wash the organic phase until neutral, and evaporate the solvent under vacuum to obtain intermediate H5-1 (93 g, yield 100%).

[0249] (2) Synthesis of intermediate H5-2:

[0250] Add H5-1 (93 g), glacial acetic acid (350 mL), and concentrated hydrochloric acid (26 mL) to a dry 1000 mL three-necked reaction flask. Stir and heat up to 100°C for reaction for 4 h. Monitor by TLC. After the raw materials are completely reacted, cool down to room temperature, pour it into ice water, extract with dichloromethane (300 mL). Wash the organic phase until neutral, evaporate the solvent under normal pressure. Dissolve the residue in absolute ethanol (170 mL) and toluene (80 mL) for crystallization, filter, and dry to obtain intermediate H5-2 (44.52 g, yield 53%).

[0251] (3) Synthesis of intermediate H5-3:

[0252] Similar to the synthesis process of intermediate H1-3, replace the raw material H1-2 with H5-2, and prepare intermediate H5-3 (48.97 g, yield 75.1%) according to the method in Preparation Example of intermediate H1-3.

[0253] (4) Synthesis of intermediate H5-4:

[0254] Similar to the synthesis process of intermediate H1-4, replace H1-3 with H5-3, and prepare intermediate H5-4 (45.96 g, yield 78.5%) according to the method in Preparation Example of intermediate H1-4.

[0255] (5) Synthesis of intermediate D-1:

[0256] Similar to the synthesis process of intermediate A-1, replace 4-iodo-3-amino-2-chloropyridine and o-chlorobenzenethiol with 2-iodo-3-amino-6-chloropyridine and o-tert-butylbenzenethiol, and prepare intermediate D-1 (23.45 g, yield 80.3%) according to the method in Preparation Example of intermediate A-1.

[0257] (6) Synthesis of Intermediate D:

[0258] Similar to the synthesis process of Intermediate A, replace Intermediate A-1 with Intermediate D-1, and prepare Intermediate D (13.63 g, yield 61.7%) according to the method in Preparation Example of Intermediate A.

[0259] (7) Synthesis of Ligand H5:

[0260] Similar to the synthesis process of Intermediate H1-5, replace Intermediate H1-4 and 1,7-dichloro-8-methylbenzo[4,5]thieno[2,3-c]pyridine with Intermediate H5-4 and Intermediate D, and prepare Ligand H5 (11.29 g, yield 55.9%) according to the method in Preparation Example of Intermediate H1-5.

[0261] MS (m / e) of Ligand H5: 407.78. 1 HNMR (400 MHz, CDCl 3 , ppm): δ

[0262] 8.30 (d, 1H), 8.19 - 8.14 (m, 1H), 8.06 (dd, 1H), 7.84 - 7.78 (m, 2H), 7.48 (t, 1H), 7.36 - 7.27 (m, 3H), 7.10 (dd, 1H), 1.63 (s, 6H), 1.43 (s, 9H).

[0263] Preparation Example 6: Synthesis of Ligand H6:

[0264]

[0265] The synthesis route is as follows:

[0266]

[0267] (1) Synthesis of Intermediate E-1:

[0268] Similar to the synthesis process of Intermediate A-1, replace 4-iodo-3-amino-2-chloropyridine and o-chlorothiophenol with 2-amino-3-iodo-6-chloropyridine and 4-tert-butylthiophenol, and prepare Intermediate E-1 (23.85 g, yield 81.7%) according to the method in Preparation Example of Intermediate A-1.

[0269] (2) Synthesis of Intermediate E:

[0270] Similar to the synthesis process of Intermediate A, replace Intermediate A-1 with Intermediate E-1, and prepare Intermediate E (14.42 g, yield 64.2%) according to the method in Preparation Example of Intermediate A.

[0271] (3) Synthesis of ligand H6:

[0272] Similar to the synthesis process of intermediate H1-5, replace intermediate H1-4 and 1,7-dichloro-8-methylbenzo[4,5]thieno[2,3-c]pyridine with intermediate H1-4 and intermediate E, and prepare ligand H6 (11.20 g, yield 62.5%) according to the method in Preparation Example of intermediate H1-5.

[0273] MS (m / e) of ligand H6: 449.65. 1 HNMR (400 MHz, CDCl 3 , ppm): δ

[0274] 8.23 - 8.11 (m, 2H), 8.08 (d, 1H), 8.03 (d, 1H), 7.95 (dd, 2H), 7.49 - 7.39 (m, 4H), 1.40 (s, 12H), 1.35 (s, 9H).

[0275] Preparation Example 7: Synthesis of ligand H7:

[0276]

[0277] The synthesis route is as follows:

[0278]

[0279] Synthesis of ligand H7:

[0280] Similar to the synthesis process of ligand H5, replace intermediate D with 1-chlorobenzofuro[2,3-c]pyridine (CAS No.: 1206975-68-9), and prepare ligand H7 (9.03 g, yield 54.3%) according to the method in Preparation Example of ligand H5.

[0281] MS (m / e) of ligand H7: 335.56. 1 HNMR (400 MHz, CDCl 3 , ppm): δ

[0282] 8.61 (d, 1H), 8.20 - 8.15 (m, 1H), 8.01 - 7.95 (m, 1H), 7.89 (d, 1H), 7.73 (d, 1H), 7.64 (dd, 1H), 7.52 - 7.30 (m, 4H), 7.11 (dd, 1H), 1.63 (s, 6H).

[0283] Preparation Example 8: Synthesis of ligand H8:

[0284]

[0285] The synthesis route is as follows:

[0286]

[0287] (1) Synthesis of intermediate H8-1:

[0288] Similar to the synthesis process of intermediate H4-4, replace intermediate H4-3 with 5-bromoacenaphthene, and prepare intermediate H8-1 (41.91 g, yield 80.9%) according to the method in Preparation Example of intermediate H4-4.

[0289] (2) Synthesis of ligand H8:

[0290] Similar to the synthesis process of ligand H4, replace intermediate H4-4 and intermediate C with H8-1 and 1-chloro[1]benzothieno[2,3-c]pyridine, and prepare ligand H8 (17.54 g, yield 53.5%) according to the method in Preparation Example of ligand H4.

[0291] MS (m / e) of ligand H8: 337.34. 1 HNMR (400 MHz, CDCl 3 , ppm): δ

[0292] 8.61 (d, 1H), 8.24 - 8.17 (m, 1H), 8.03 - 7.96 (m, 2H), 7.89 (d, 1H), 7.83 (d, 1H), 7.52 - 7.40 (m, 3H), 7.36 - 7.24 (m, 2H), 3.36 (d, 4H).

[0293] Preparation Example 9: Synthesis of ligand H9:

[0294]

[0295] The synthesis route is as follows:

[0296]

[0297] (1) Synthesis of intermediate H9-1:

[0298] Similar to the synthesis process of intermediate H2-6, replace intermediate A with 1,8-dichlorobenzo[4,5]thieno[2,3-c]pyridine, and prepare intermediate H9-1 (19.14 g, yield 85.4%) according to the method in Preparation Example of intermediate H2-6.

[0299] (2) Synthesis of ligand H9:

[0300] Similar to the synthesis process of ligand H2, replace intermediate H2-6 and 4-tert-butylphenylboronic acid with H9-1 and phenyl-D5-boronic acid, and prepare ligand H9 (11.35 g, yield 53.6%) according to the method in Preparation Example of ligand H2.

[0301] MS (m / e) of ligand H9: 488.87. 1 HNMR (400 MHz, CDCl 3 , ppm): δ

[0302] 8.62 (d, 1H), 8.14 (dt, 1H), 8.05 (dt, 1H), 7.87 - 7.81 (m, 3H), 7.53 (t, 1H), 7.45 - 7.35 (m, 2H), 7.31 (dd, 1H), 2.16 (s, 1H), 2.00 (s, 1H), 1.36 (d, 12H).

[0303] Preparation Example 10: Synthesis of ligand H10:

[0304]

[0305] The synthesis route is as follows:

[0306]

[0307] (1) Synthesis of intermediate F-1:

[0308] Similar to the synthesis process of intermediate C-1, replace o-methoxyphenylboronic acid with 2,4-di-tert-butyl-6-methoxyphenylboronic acid (CAS No.: 175602-46-7), and prepare intermediate F-1 (50.98 g, yield 58.9%) according to the method in Preparation Example of intermediate C-1.

[0309] (2) Synthesis of intermediate F:

[0310] Similar to the synthesis process of intermediate C, replace intermediate C-1 with intermediate F-1, and prepare intermediate F (25.67 g, yield 55.3%) according to the method in Preparation Example of intermediate C.

[0311] (3) Synthesis of ligand H10:

[0312] Similar to the synthesis process of intermediate H1-5, replace 1,7-dichloro-8-methylbenzo[4,5]thieno[2,3-c]pyridine with intermediate F, and prepare ligand H10 (10.03 g, yield 51.4%) according to the method in Preparation Example of intermediate H1-5.

[0313] MS (m / e) of ligand H10: 489.76.1 HNMR (400 MHz, CDCl 3 , ppm): δ 8.78 (s, 1H), 8.23 - 8.17 (m, 1H), 7.96 (d, 1H), 7.81 (s, 1H), 7.49 - 7.31 (m, 5H), 1.43 (s, 9H), 1.40 (s, 12H), 1.36 (s, 9H).

[0314] Example 1: Synthesis of Compound 14

[0315]

[0316] (1) Synthesis of Intermediate 14-1:

[0317] Under nitrogen protection, ligand H1 (10 g) and ethylene glycol monoethyl ether (100 mL) were added to a dry 250 mL single-necked reaction flask. Iridium(III) chloride hydrate (2.95 g) and deionized water (30 mL) were added with stirring. The reaction was refluxed for 24 h in the dark and then cooled to room temperature. Deionized water (100 mL) was added to the reaction system, and the mixture was stirred for 30 minutes and then filtered by suction. The filter cake was added to anhydrous ethanol (50 mL), sonicated for 5 minutes, filtered by suction, added to ethyl acetate (50 mL), refluxed and slurried, and then filtered by suction to obtain Intermediate 14-1 (8.0 g, yield 86%).

[0318] (2) Synthesis of Compound 14:

[0319] Under nitrogen protection, Intermediate 14-1 (8.0 g) and ethylene glycol monoethyl ether (80 mL) were added to a dry 250 mL single-necked reaction flask. Starting material I (2.18 g) and anhydrous sodium carbonate (1.02 g) were added with stirring. The reaction was refluxed for 24 h in the dark and then cooled to room temperature. Deionized water (100 mL) was added to the reaction system, and the mixture was stirred for 30 minutes and then filtered by suction. The filter cake was added to anhydrous ethanol (50 mL), sonicated for 5 minutes, filtered by suction, added to dichloromethane (15 mL), refluxed and slurried, filtered at room temperature, and the product was dissolved in dichloromethane for column chromatography. The eluent was concentrated and the solvent was removed. The residue was added to dichloromethane (15 mL), slurried, filtered at room temperature, added to n-heptane (15 mL), slurried at room temperature, and filtered by suction to obtain Compound 14 (6.22 g, yield 67.5%).

[0320] MS (m / e) of Compound 14: 1356.60. 1 HNMR (400 MHz, CDCl 3, ppm): δ 8.58 (d, 2H), 7.89 - 7.83 (m, 4H), 7.72 (d, 2H), 7.52 - 7.46 (m, 4H), 7.30 (s, 2H), 7.11 (d, 2H), 5.65 - 5.61 (m, 1H), 2.65 (s, 4H), 2.45 - 2.35 (m, 8H), 1.56 - 1.43 (m, 8H), 1.40 (d, 24H), 0.94 - 0.86 (m, 30H).

[0321] Example 2 - 9:

[0322] The following compounds were prepared using a synthetic method similar to that for preparing Compound 14, with the difference that the ligand and / or starting material I were different. The ligand, starting material I, target product, and mass spectrometry and NMR characterization data are shown in Table 3A:

[0323] Table 3A

[0324]

[0325]

[0326] Example 10: Synthesis of Compound 125

[0327] (1) Synthesis of Intermediate 125 - 1:

[0328] In a 100 mL three - necked flask equipped with a mechanical stirrer, reflux condenser, and nitrogen protection device, raw material J (3.67 g), iridium(III) chloride trihydrate (2.10 g), ethylene glycol monoethyl ether (45 mL), and water (15 mL) were added in sequence. Under nitrogen protection, it was heated to 110 °C and refluxed for 24 h. After natural cooling, water (10 mL) was added, stirred for 10 min, and then filtered by suction. It was washed successively with water and ethanol. Dried in vacuo to obtain Intermediate 125 - 1 (4.17 g, yield 78.7%).

[0329] (2) Synthesis of Intermediate 125 - 2:

[0330] In a 500 mL three - necked flask equipped with a nitrogen protection device, Intermediate 125 - 1 (3.56 g) was added, followed by dichloromethane (50 mL). After stirring well, a methanol solution (50 mL) of silver trifluoromethanesulfonate (1.6 g) was added, and it was stirred for 24 h under light - protected conditions. After cooling to room temperature, it was filtered through diatomaceous earth, and the filtrate was concentrated to dryness to obtain Intermediate 125 - 2. This solid was used directly in the next step without further treatment.

[0331] (3) Synthesis of Compound 125:

[0332] In a 250 mL three-necked flask, add intermediate 125-2 (6.25 g) and ligand H1 (10 g), then add ethanol (150 mL). Heat this mixture under reflux for 36 h, cool the reactant to room temperature, filter, then dissolve it in dichloromethane and separate by column chromatography to obtain compound 125 (4.21 g, yield 52.0%).

[0333] The MS (m / e) of compound 125: 1157.67. The 1 HNMR (400 MHz, CDCl 3 , ppm): δ 8.58 (d, 1H), 8.45 - 8.41 (m, 2H), 8.23 - 8.17 (m, 2H), 7.89 - 7.83 (m, 2H), 7.75 - 7.69 (m, 3H), 7.64 - 7.34 (m, 18H), 7.32 (s, 1H), 7.11 (d, 1H), 2.65 (s, 2H), 2.44 (s, 3H), 2.31 (d, 6H), 1.40 (d, 12H), 0.89 (s, 9H).

[0334] Examples 11 - 12:

[0335] The following compounds were prepared using a synthetic method similar to that for preparing compound 125, with the difference being that the ligand and / or raw material J were different. The ligand, raw material J, target product, and mass spectrometry and 1 HNMR characterization data are shown in Table 3B:

[0336] Table 3B

[0337]

[0338]

[0339] The present invention exemplarily gives the specific synthetic methods for the above several compounds. For other organic compounds for which no specific synthetic methods are given, they are also prepared by similar methods, and can be obtained only by replacing the raw materials, which will not be elaborated here. Alternatively, those skilled in the art can also prepare them by other methods in the prior art.

[0340] The present invention also discloses the use of the above-mentioned luminescent compound in the preparation of an organic electroluminescent device. The organic electroluminescent device of the present invention has the same structure as the organic electroluminescent device in the prior art, including an anode layer, a plurality of light-emitting functional layers, and a cathode layer; the plurality of light-emitting functional layers at least include a light-emitting layer, and the light-emitting functional layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, and an electron transport layer, wherein the light-emitting layer contains the above-mentioned organic compound of the present invention.

[0341] In an embodiment of specifically preparing an organic electroluminescent device, a substrate may be used below the anode or above the cathode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, waterproofness, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate for display use.

[0342] The anode can be formed by sputtering or depositing a material used as the anode on the substrate. Oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 )), zinc oxide (ZnO), etc. and any combination thereof can be used. The cathode material can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. and any combination between them.

[0343] The following are examples of organic electroluminescent devices prepared by the present invention using representative compounds of the present invention:

[0344] Device Example

[0345] This example provides an OLED device, and the device structure (materials and layer thicknesses used for each functional layer) is: ITO / HATCN (10 nm) / HT01 (60 nm) / TAPC (10 nm) / RH: 2% of the dye material compound of the present invention (40 nm) / TPBI (5 nm) / ET01:LiQ (6:4) (35 nm) / LiQ (1 nm) / Al.

[0346] The molecular structures of the materials for each functional layer are as follows:

[0347]

[0348]

[0349] Device Example 1:

[0350] (1) The glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol (volume ratio 1:1), baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface;

[0351] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate to 5×10 -5 ~9×10 -3Pa, HATCN was vacuum-evaporated on the above-mentioned anode layer film as a hole injection layer at an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 10 nm; then the first hole transport layer HT01 was evaporated at an evaporation rate of 0.1 nm / s and a thickness of 60 nm; then the second hole transport layer TAPC was evaporated at an evaporation rate of 0.1 nm / s and an evaporation film thickness of 10 nm;

[0352] (3) On top of the hole transport layer, EML was vacuum-evaporated as the light-emitting layer of the device. EML includes the host material RH and the dye material compound 14 of the present invention with a doping concentration of 2% to form the organic light-emitting layer of the device. The evaporation rates were 0.098 nm / s and 0.002 nm / s respectively, and the total evaporation film thickness was 40 nm; then 5 nm of TPBI was evaporated to form a hole blocking layer at an evaporation rate of 0.1 nm / s;

[0353] (4) Then, ET01:LiQ with a mass ratio of 6:4 was evaporated on top of the hole blocking layer as the electron transport material of the device's electron transport layer. The evaporation rates were 0.06 nm / s and 0.04 nm / s respectively, and the total evaporation film thickness was 35 nm;

[0354] (5) On the electron transport layer, 1 nm of LiQ was successively vacuum-evaporated as the electron injection layer, and a 150 nm thick Al layer was evaporated as the cathode of the device.

[0355] Device Examples 2 - 12, Device Comparative Examples 1 - 4:

[0356] An organic electroluminescent device, which is only different from Device Example 1 in that the dye materials of the light-emitting layer are the compounds shown in Table 4; other layers, thicknesses, materials, and preparation methods are the same as those of Device Example 1.

[0357] The structures of the dye material compounds in Device Comparative Examples 1 - 4 are as follows:

[0358]

[0359]

[0360] The performance test data of the organic electroluminescent devices prepared in the above Device Examples 1 - 12 and Device Comparative Examples 1 - 4 of the present invention are shown in Table 4 below.

[0361] Table 4

[0362]

[0363] As can be seen from the above results, compared with compounds D-01, D-02, D-03, and D-04, the current efficiency of the corresponding devices 1-12 prepared from the metal-organic complexes provided by the present invention has been improved, the operating voltage has been significantly reduced, and the lifespan has also been extended.

[0364] Although the present invention has been described in detail above with general descriptions, specific embodiments, and experiments, modifications or improvements can be made to it based on the present invention, which are obvious to those skilled in the art. Therefore, these modifications or improvements made without departing from the spirit of the present invention all fall within the scope of protection required by the present invention.

Claims

1. A metal organic complex comprising a metal atom M and a first ligand L coordinated with the metal atom M a ,in, The first ligand L a The structure is shown in formula (I): In formula (I), R1 and R2 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and R1 and R2 are not connected or connected to form a ring through a chemical bond; Z1-Z4 are independently selected from CR Z or N; U1-U4 are independently selected from C, CR U1 or N, and any two adjacent ones of U1-U4 are C and fused to form a ring with formula (Ia); in formula (Ia), -* represents the connection site with formula (I); U5-U8 are independently selected from CR U2 or N; X is selected from any one of CRx1Rx2, NRx3, SiRx4Rx5, S, O or Se; The R Z , R U1 , R U2 are independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, ester, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy; any two adjacent R Z are not connected or connected to form a ring through chemical bonds; any two adjacent R U1 are not connected or connected to form a ring through chemical bonds; any two adjacent R U2 They are not connected to each other or connected to form a ring through chemical bonds; The Rx1, Rx2, Rx3, Rx4, and Rx5 are each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, and the Rx1 and Rx2 or Rx4 and Rx5 are not connected or connected to form a ring through a chemical bond; R1, R2, R Z , R U1 , R U2 When Rx1, Rx2, Rx3, Rx4, and Rx5 contain one or more substituents, the substituents are independently selected from any one of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl, or a combination of at least two thereof; when there are multiple substituents, any two adjacent substituents are not connected or are connected to form a ring through a chemical bond; The dotted line represents the ligand L a The binding site with the metal atom M; n is 1, 2, 3, 4, 5, 6, 7 or 8.

2. The metal-organic complex according to claim 1, characterized in that R1 and R2 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl; Preferably, R1 and R2 are each independently selected from hydrogen, deuterium, or any one of the following substituted or unsubstituted groups: C1-C6 straight or branched chain alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C12 aryl, C3-C12 heteroaryl; Preferably, R1 and R2 are each independently selected from hydrogen, deuterium, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, methoxy, ethoxy, -O-propyl, -O-isopropyl, -O-butyl, -O-tert-butyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrolyl, tetrahydropyranyl, phenyl, naphthyl, biphenyl, pyridyl, furyl, thienyl; Preferably, when R1 and R2 contain one or more substituents, the substituents are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, C6-C10 aryl, and C3-C10 heteroaryl; More preferably, when R1 and R2 contain one or more substituents, the substituents are each independently selected from deuterium, fluorine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl or phenyl; Further preferably, when R1 and R2 contain two or more substituents, any two adjacent substituents are not connected or are connected by chemical bonds to form a 5-6 membered ring; Preferably, R1 and R2 are each independently selected from hydrogen, deuterium, or any one of the following groups: *-CH3, *-CH3, *-C2D5, 3. The metal-organic complex according to claim 1 or 2, characterized in that: R Z , R U1 and R U2 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C3-C20 heteroarylamino; Preferably, R Z , R U1 and R U2 Each is independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following substituted or unsubstituted groups: C1-C6 straight or branched alkyl, C1-C6 alkoxy, C1-C6 alkylsilyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C15 aryl, C3-C15 heteroaryl, C6-C15 arylamino, C3-C15 heteroarylamino; Preferably, R Z , R U1 and R U2 Each is independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following groups which are substituted or unsubstituted: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, methoxy, ethoxy, -O-propyl, -O-isopropyl, -O-butyl, -O-tert-butyl, trimethylsilyl, di(ethyl)methylsilyl, triethylsilyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, 1,4,4-trimethylcyclohexyl, tetrahydropyrrolyl, tetrahydropyranyl, phenyl, naphthyl, biphenyl, fluorenyl, 9,9-dimethylfluorenyl, pyridyl, furanyl, thienyl, dibenzofuran, dibenzothiophene, carbazolyl, diphenylamino, dipyridylamino; Preferably, when R Z , R U1 and R U2 When R contains one or more substituents, the substituents are independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, C6-C10 aryl, and C3-C10 heteroaryl. More preferably, when R Z , R U1 and R U2 When R contains one or more substituents, the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl or phenyl; further preferably, when R Z , R U1 and R U2 When there are two or more substituents, any two adjacent substituents are not connected or connected by chemical bonds to form a 5-6 membered ring; Preferably, R Z , R U1 and R U2 Each independently selected from hydrogen, deuterium, fluorine, cyano or any one of the following groups: *-CH3, *-CF3, *-CD3, 4. The metal-organic complex according to any one of claims 1 to 3, characterized in that The first ligand L a It has a structure shown in any one of formula (II-1) to formula (II-6): Wherein, R1, R2, n, and X are defined as in formula (I); R Za -R Zd The definition of R is the same as that of R in formula (I) Z Definition, R U1a -R U1d The definition of R is the same as that of R in formula (I) U1 Definition, R U2a -R U2d The definition of R is the same as that of R in formula (I) U2 Definition of; Preferably, R1 and R2 are independently selected from any one of hydrogen, deuterium, C1-C6 straight chain or branched alkyl, deuterated C1-C6 straight chain or branched alkyl; More preferably, R1 and R2 are independently selected from any one of hydrogen, deuterium or the following groups: *-CH3, *-CD3, Preferably, R Za -R Zd is independently selected from any one of hydrogen, deuterium, C1-C6 straight chain or branched alkyl, deuterated C1-C6 straight chain or branched alkyl; more preferably, R Za -R Zd Any one independently selected from hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, propyl, deuterated propyl, isopropyl, deuterated isopropyl, butyl, deuterated butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl; Preferably, R U1a -R U1d is independently selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 straight or branched alkyl, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl; more preferably, R U1a -R U1d Independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following groups: *-CH3, *-CF3, *-CD3, Preferably, X is selected from any one of S, O or Se, more preferably S or O; Preferably, n is 1, 2 or 3.

5. The metal-organic complex according to any one of claims 1 to 4, characterized in that: The first ligand L a Has any of the structures shown below, wherein X is selected from S, O or Se:

6. The metal-organic complex according to any one of claims 1 to 5, characterized in that: The metal complex further comprises a second ligand L coordinated with the metal atom M b and / or a third ligand L c The structural formula of the metal complex is M(L a ) i (L b ) j (L c ) k ; wherein i is selected from 1 or 2, j is selected from 0, 1 or 2, and k is selected from 0 or 1; the sum of i, j, and k is equal to the oxidation state of M; The second ligand L b and the third ligand L c are independently selected from the structures represented by formula (III) and formula (IV): Among them, R3~R 10 are independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-20 alkoxy, substituted or unsubstituted C1-20 alkylsilyl, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C3-30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, wherein R3 to R 10 The two adjacent groups are not connected or connected to form a ring through chemical bonds; R 31 ~R 37 are independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-20 alkoxy, substituted or unsubstituted C1-20 alkylsilyl, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C3-30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, wherein R 31 ~R 37 The two adjacent groups are not connected or connected to form a ring through chemical bonds; When R3~R 10 , R 31 ~R 37 When there is one or more substituents in the formula (a), the substituents are each independently selected from any one of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl, or a combination of at least two thereof; Preferably, R3~R 10 are independently selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 straight or branched alkyl, substituted or unsubstituted C1-C6 alkylsilyl, substituted or unsubstituted C6-C12 aryl; more preferably, R3 to R 10 Each of the following is independently selected from any one of hydrogen, deuterium, fluorine, cyano, trifluoromethyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated isobutyl, deuterated tert-butyl, trimethylsilyl, triethylsilyl, phenyl and deuterated phenyl; Preferably, R 31 ~R 37 are independently selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 straight or branched alkyl, substituted or unsubstituted C3-C8 cycloalkyl; more preferably, R 31 ~R 37 any one independently selected from hydrogen, deuterium, fluorine, cyano, trifluoromethyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, 3-methylpentyl, 2,4-dimethylpentyl, 2,2,4,4-tetramethylpentyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated isobutyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, cyclopentyl substituted by one or more substituents selected from deuterium, fluorine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, cyclohexyl substituted by one or more substituents selected from deuterium, fluorine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; Preferably, the L b , L c Each is independently selected from any one of the following structures: The dotted line represents the binding site between the ligand and the metal atom M.

7. The metal-organic complex according to any one of claims 1 to 6, characterized in that: The metal atom M is selected from Cu, Pt, Au, Ru, Pd, Rh or Ir; preferably Pt or Ir, more preferably Ir; and / or The metal organic complex is selected from the following structures shown in Compound 1 to Compound 160, wherein Compound 1 to Compound 120 have Ir(L a )2(L b ) or Ir(L a )2(L c ) structure, where two L a Same, L a , L b or L c The corresponding structures are selected from the following table: Compounds 121 to 160 have Ir(L a )(L b )2 structure, where two L b Same, L a and L b The corresponding structures are selected from the following table:

8. Use of the metal organic complex according to any one of claims 1 to 7 in organic electronic devices; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the metal organic complex is used as a luminescent dye in the organic electronic device; Preferably, the metal organic complex is used as a dye material of a host material in the organic electroluminescent device.

9. An organic electroluminescent device, comprising a light-emitting layer, wherein the light-emitting layer comprises the metal organic complex according to any one of claims 1 to 7; Preferably, the organic electroluminescent device comprises a substrate, and an anode layer, a plurality of light-emitting unit layers and a cathode layer sequentially formed on the substrate, wherein: The light-emitting unit layer includes a light-emitting layer; Preferably, the organic electroluminescent device further comprises one or more of a hole injection layer, a hole transport layer, an electron transport layer, and an electron blocking layer; Preferably, the doping concentration of the metal organic complex in the host material of the light-emitting layer is 1 to 12 wt %, preferably 1 to 8 wt %, and more preferably 2 to 7 wt %. 10 . A display device or a lighting device, comprising the organic electroluminescent device according to claim 9 .

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