Organic metal complex and application thereof

Abstract

The invention provides an organic metal complex. The organic metal complex has a structure as shown in a formula (I). The organic metal complex provided by the invention is applied to the organic light-emitting device, and the prepared organic light-emitting device shows excellent performance of high efficiency and long service life. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent display, and in particular relates to an organic metal complex and also relates to the application of the organic electroluminescent complex in an organic electroluminescent device. Background Art

[0002] Organic light-emitting diodes (OLEDs) emit light in two ways: fluorescence and phosphorescence. Theoretically, the ratio of singlet excited states to triplet excited states, caused by charge re-binding, is 1:3. In 1998, Professors Baldo and Forrest discovered that triplet phosphorescence can be exploited at room temperature, raising the upper limit of internal quantum efficiency to 100%. Triplet phosphorescent materials are often complexes composed of heavy metal atoms. By leveraging the heavy atom effect and strong spin-orbit coupling, they cause intermixing of the singlet and triplet excited states, releasing the previously forbidden triplet energy into phosphorescence, significantly improving quantum efficiency.

[0003] However, currently, OLEDs made from organometallic complexes have low lifespan, efficiency, and stability. Therefore, how to design materials with better performance has always been a pressing issue for those skilled in the art. Summary of the Invention

[0004] In view of the above problems in the prior art, the object of the present invention is to provide a new organometallic complex, which is applied to organic electroluminescent devices. The prepared organic electroluminescent devices exhibit excellent performance of high efficiency and long life.

[0005] In a first aspect, the present invention provides an organometallic complex having a structure shown in formula (I):

[0006]

[0007] In formula (I), M is selected from metals with a relative atomic mass greater than 40;

[0008] Q1-Q3 are each independently selected from C or N;

[0009] L is selected from a single bond, O, S, S=O, SO2, Se, Se=O, SeO2, SiR L1 R L2 NR L3 , CR L4 R L5 、C=O、GeR L6 R L7 PR L8 、

[0010] RL9 P=O、BR L10 Any of the following;

[0011] A1-A8 are each independently selected from CR A or N;

[0012] Z1-Z8 are each independently selected from CR Z or N;

[0013] M1-M8 are each independently selected from CR M or N;

[0014] R N 、R L1 -R L10 、R A 、R Z 、R M are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, ester, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, 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, substituted or unsubstituted C6-C30 arylthio, and substituted or unsubstituted C3-C30 heteroarylthio; said R N 、R L1 -R L10 、R A 、R Z 、R M Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds;

[0015] The R N 、R L1 -R L10 、R A 、R Z 、R MThe substituents substituted in the alkyl group are each independently selected from any one of deuterium, halogen, cyano, nitro, hydroxyl, ester, amino, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, and C3-C30 heteroarylthio; and the substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0016] In some embodiments, at most 2 (e.g., 0, 1, 2) of A1, A2, A3, and A4 are selected from N, and the rest are independently selected from CR A and / or at most 2 (e.g. 0, 1, 2) of A5, A6, A7, and A8 are selected from N, and the rest are independently selected from CR A .

[0017] In some preferred embodiments, one of A1, A2, A3, and A4 is selected from N, and the others are independently selected from CR A and / or one of A5, A6, A7, and A8 is selected from N, and the others are each independently selected from CR A .

[0018] In some preferred embodiments, A1, A2, A3, A4, A5, A6, A7, and A8 are each independently selected from CR A Multiple (e.g. 2, 3, 4, 5, 6, 7, 8) CRs A R in A are the same or different groups.

[0019] In some preferred embodiments, the number of CH in A1, A2, A3, A4, A5, A6, A7, and A8 is 1-8 (e.g., 1, 2, 3, 4, 5, 6, 7, 8).

[0020] In some preferred embodiments, the R Aand each is independently selected from hydrogen, deuterium, halogen (e.g., F, Cl, Br, I), cyano, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, substituted or unsubstituted C6-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) for example, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino, substituted or unsubstituted C3-C30 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino, substituted or unsubstituted C6-C30 (for example, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy, substituted or unsubstituted C3-C30 (for example, any one of C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryloxy, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) arylthio, substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylthio; the R A Each independently is not connected to the adjacent groups or is connected by chemical bonds to form a ring.

[0021] Preferably, the R AEach is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 arylamino, and substituted or unsubstituted C3-C20 heteroarylamino.

[0022] In some preferred embodiments, the R A The substituents substituted in the present invention are each independently selected from deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) , C7, C8, C9, etc.) cycloalkyl, C2-C10 (for example, C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, C6-C30 (for example, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, C3-C30 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two thereof.

[0023] Preferably, the R A The substituents substituted in the alkyl group are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl.

[0024] In the present invention, R A The adjacent groups are connected to form a ring through chemical bonds. A It is not only connected to the C atom by chemical bonds, but also to adjacent groups (such as R A With the adjacent R in A2 A Or with adjacent R N ) are connected by chemical bonds (such as single bonds, double bonds, C, O, S or N, etc.) to form a fused ring structure. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0025] In some preferred embodiments, the RA Each is independently selected from hydrogen, deuterium, halogen, cyano, or any of the following groups which may be substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, isopentyl, tert-pentyl, neopentyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl, tetrahydrothiopyranyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, 2,3-dihydroindanyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, pyridyl, furanyl, benzofuranyl, dibenzofuranyl, benzonaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, benzonaphthothienyl, carbazolyl, N-phenylcarbazolyl, (Ar1 and Ar2 are each independently selected from any one of phenyl, naphthyl, pyridyl, dibenzofuranyl and dibenzothiophenyl).

[0026] In some preferred embodiments, the R A The substituted substituents are each independently selected from any one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, and pyridyl.

[0027] Specifically, the combined substituents may include, for example, deuterated alkyl formed by a combination of alkyl and deuterium (e.g., deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, etc.); halogenated alkyl formed by a combination of halogen and alkyl (e.g., trifluoromethyl, etc.); aryl formed by a combination of aryl and deuterium (e.g., deuterated phenyl, etc.); alkyl-substituted aryl formed by a combination of alkyl and aryl (e.g., tert-butylphenyl, 2,2-dimethyl-1,3-dihydroindenyl, 1,1,3,3-tetramethyl-2,3-dihydroindenyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, etc.) or aryl-substituted alkyl (e.g., tert-butyl substituted with phenyl, etc.). The following descriptions shall have the same meanings and shall not be repeated one by one.

[0028] In some preferred embodiments, the adjacent R A They are not connected or are connected by chemical bonds to form a substituted or unsubstituted C3-C10 (for example, C4, C5, C6, C7, C8, C9, etc.) alicyclic ring, a substituted or unsubstituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring, or a substituted or unsubstituted C3-C20 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring.

[0029] In some preferred embodiments, the substituted substituents in the above-mentioned ring "substituted or unsubstituted" are each independently selected from any one or a combination of at least two of deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C6 (e.g., C2, C3, C4, C5, etc.) alkyl, C3-C8 (e.g., C4, C5, C6, C7, etc.) cycloalkyl, C6-C12 (e.g., C6, C9, C10, etc.) aryl, C3-C12 (e.g., C3, C4, C5, C6, C9, C10, etc.) heteroaryl.

[0030] In some preferred embodiments, the adjacent R A They are not connected or connected to form a ring (e.g. The ring is optionally substituted with any one or at least two substituents selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl.

[0031] In some embodiments, at most one (eg, 0 or 1) of Z1, Z2, Z3, and Z4 is selected from N, and the rest are independently selected from CR Z and / or at most one (e.g., 0 or 1) of Z5, Z6, Z7, and Z8 is selected from N, and the rest are each independently selected from CR Z .

[0032] In some preferred embodiments, Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are each independently selected from CR Z Multiple (e.g. 2, 3, 4, 5, 6, 7, 8) CRs Z R in Z are the same or different groups.

[0033] In some preferred embodiments, the number of CH in Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is 1-8 (e.g., 1, 2, 3, 4, 5, 6, 7, 8).

[0034] In some preferred embodiments, the R Z Each is independently selected from any one or a combination of at least two of hydrogen, deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C6 (e.g., C2, C3, C4, C5, etc.) alkyl, C2-C6 (e.g., C3, C4, C5, etc.) alkenyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl; said R ZEach independently is not connected to the adjacent groups or is connected by chemical bonds to form a ring.

[0035] In some preferred embodiments, the R Z Each is independently selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, methyl, tert-butyl, phenyl, naphthyl, and pyridyl. More preferably, the R Z are all selected from hydrogen.

[0036] In some embodiments, at most one (eg, 0 or 1) of M1 and M2 is selected from N, and the rest are independently selected from CR M and / or at most 1 (eg 0 or 1) of M3, M4, M5, and M6 is selected from N, and the rest are independently selected from CR M and / or at most 1 (eg 0 or 1) of M7 and M8 is selected from N, and the rest are independently selected from CR M .

[0037] In some preferred embodiments, M1, M2, M3, M4, M5, M6, M7, and M8 are each independently selected from CR M Multiple (e.g. 2, 3, 4, 5, 6, 7, 8) CRs M R in M are the same or different groups.

[0038] In some preferred embodiments, the number of CH in M1, M2, M3, M4, M5, M6, M7, and M8 is 1-8 (e.g., 1, 2, 3, 4, 5, 6, 7, 8). Preferably, M1, M2, M3, M4, M5, and M8 are selected from CH, and M6 and M7 are each independently selected from CR M .

[0039] In some preferred embodiments, the R M Each is independently selected from any one or a combination of at least two of hydrogen, deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl; said R M Each independently is not connected to the adjacent groups or is connected by chemical bonds to form a ring.

[0040] In some preferred embodiments, the R M Each is independently selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, and pyridyl.

[0041] In some preferred embodiments, R in M6 M and R in M7 M They are not connected or are connected by chemical bonds to form substituted or unsubstituted C4-C10 (such as C5, C6, C7, C8, C9, etc.) alicyclic rings, or substituted or unsubstituted C3-C10 (such as C4, C5, C6, C7, C8, C9, etc.) alicyclic rings.

[0042] In some preferred embodiments, the substituted substituents in the above-mentioned ring "substituted or unsubstituted" are each independently selected from any one or a combination of at least two of deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C6 (e.g., C2, C3, C4, C5, etc.) alkyl, C3-C8 (e.g., C4, C5, C6, C7, etc.) cycloalkyl, C6-C12 (e.g., C6, C9, C10, etc.) aryl, C3-C12 (e.g., C3, C4, C5, C6, C9, C10, etc.) heteroaryl.

[0043] In some preferred embodiments, R in M6 M and R in M7 M They are not connected or connected to form a ring through chemical bonds (e.g.

[0044] The ring is optionally substituted with any one or at least two substituents selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl.

[0045] In some embodiments, R N is selected from any one of deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, wherein R N It is not connected to adjacent groups or is connected to form a ring through chemical bonds.

[0046] In some preferred embodiments, the R NThe substituents substituted in the above-mentioned compound are each independently selected from any one of deuterium, halogen, cyano, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl, or a combination of at least two thereof.

[0047] In some preferred embodiments, the R N selected from deuterium, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) ) heterocycloalkyl, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.), wherein R N It is not connected to adjacent groups or is connected to form a ring through chemical bonds.

[0048] Preferably, the R N Any one selected from deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0049] In some preferred embodiments, the R NThe substituents substituted in the present invention are each independently selected from deuterium, halogen (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) C7, C8, C9, etc.) heterocycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two thereof.

[0050] Preferably, the R N The substituents substituted in the above-mentioned compound are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C2-C8 heterocycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl.

[0051] In some preferred embodiments, the R N deuterium, or any of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, isopentyl, tert-pentyl, neopentyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl, tetrahydrothiopyranyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, naphthylphenyl, phenylnaphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, fluorenyl, spirofluorenyl, benzofluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, furyl, benzofuranyl, dibenzofuranyl, benzonaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, benzonaphthothienyl, N-phenylcarbazolyl.

[0052] In some preferred embodiments, the R N The substituents substituted in the above-mentioned group are each independently selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, and carbazolyl, or a combination of any one or two thereof.

[0053] In some embodiments, the L is selected from a single bond, O, S, Se, SiRL1 R L2 NR L3 , CR L4 R L5 BR L10 Any one of the following; where R L1 、R L2 、R L3 、R L4 、R L5 、R L10 Each is independently selected from any one or a combination of at least two of C1-C6 (e.g., C2, C3, C4, C5, etc.) alkyl, C3-C8 (e.g., C4, C5, C6, C7, etc.) cycloalkyl, C2-C8 (e.g., C3, C4, C5, C6, C7, etc.) heterocycloalkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, and R L1 、R L2 、R L3 、R L4 、R L5 、R L10 Each independently is not connected to the adjacent groups or is connected by chemical bonds to form a ring.

[0054] Preferably, the R L1 、R L2 、R L3 、R L4 、R L5 、R L10 Each is independently selected from any one or a combination of two of methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl.

[0055] Preferably, the L is selected from a single bond, O, S, SiR L1 R L2 NR L3 , CR L4 R L5 More preferably, the L is selected from a single bond, O, and S. Further, the L is selected from O.

[0056] In some embodiments, the M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, or Pt. Preferably, the M is selected from Pt or Pd. More preferably, the M is selected from Pt.

[0057] In some embodiments, Q1 is selected from N, Q2, and Q3 are both selected from C.

[0058] In some embodiments, the organometallic complex has a structure represented by formula (II-1) or formula (II-2):

[0059]

[0060] In formula (II-1) and formula (II-2), M, L, and R N The same definition as in formula (I) applies.

[0061] R A1 、R A2 、R Z1 、R Z2 、R M1 、R M2 、R M2’ Each independently represents no substitution, monosubstitution to the maximum allowed substitution.

[0062] Among them, R A1 Indicates no substitution (R A1 is hydrogen), monosubstituted, disubstituted, trisubstituted or tetrasubstituted; when R A1 When it represents disubstituted, trisubstituted, or tetrasubstituted, multiple R A1 are the same or different groups; R A2 、R Z1 、R Z2 、R M1 、R M2 、R M2’ The same applies to the expression of , and for the sake of brevity, I will not elaborate on it.

[0063] The R A1 、R A2 、R Z1 、R Z2 、R M1 、R M2 、R M2’ are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, 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, substituted or unsubstituted C6-C30 arylthio, and substituted or unsubstituted C3-C30 heteroarylthio; said R A1 、R A2 、R Z1 、RZ2 、R M1 、R M2 、R M2’ Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds;

[0064] The R A1 、R A2 、R Z1 、R Z2 、R M1 、R M2 、R M2’ The substituents substituted in the alkyl group are each independently selected from any one of deuterium, halogen, cyano, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, and C3-C30 heteroarylthio, or a combination of at least two thereof; the substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0065] In formula (II-2), ring A is selected from a substituted or unsubstituted C4-C10 alicyclic ring, or a substituted or unsubstituted C3-C10 alicyclic heterocyclic ring;

[0066] Wherein, the substituents substituted in the ring A are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl.

[0067] In some preferred embodiments, ring A is selected from

[0068] wherein the dotted line represents a fused bond. wherein the ring A is optionally substituted by any one or at least two substituents selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl.

[0069] In some embodiments, the organometallic complex is selected from the group consisting of:

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] The organometallic complex provided by the present invention can be used as a phosphorescent dye (also known as a luminescent material, dye, doping material, or dopant, etc.), and can effectively solve the problems of currently commonly used phosphorescent dyes in terms of color purity, luminous efficiency, and lifespan. Organic electroluminescent devices prepared using the organometallic complex of the present invention exhibit superior performance of high efficiency and long lifespan.

[0083] Specifically, the organometallic complex material provided by the present invention has the following advantages:

[0084] The present invention improves the conjugation effect by introducing suitable groups (i.e., indole (3,2,1-JK) carbazole groups and benzo [C] carbazole groups), thereby imparting higher stability and triplet energy levels, as well as better carrier mobility and the ability to match adjacent energy levels. Application of the phosphorescent dye in OLED devices can effectively improve the efficiency and lifespan of the devices.

[0085] In a second aspect, the present invention provides use of the above-mentioned organometallic complex in the preparation of organic electronic devices.

[0086] In some embodiments, the organic electronic device includes an organic electroluminescent 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 electronic paper. Most preferably, the organic electroluminescent device is suitable.

[0087] In some embodiments, the organometallic complex is used as a phosphorescent dye as a host material in an organic electroluminescent device. The electroluminescent device prepared using the organometallic complex of the present invention exhibits superior performance of high purity, high brightness, and high efficiency.

[0088] In a third aspect, the present invention provides an organic electroluminescent device comprising a substrate and an anode layer, one or more light-emitting unit layers and a cathode layer sequentially formed on the substrate; the light-emitting unit layer comprises a light-emitting layer, and the phosphorescent dye in the light-emitting layer comprises the organic metal complex.

[0089] In some embodiments, the light-emitting unit layer further comprises one or more of a hole injection layer, a hole transport layer, an electron transport layer, and an electron blocking layer. The hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, and the cathode layer is formed on the electron transport layer. Multiple light-emitting layers are provided between the hole transport layer and the electron transport layer. Preferably, the phosphorescent dye in the light-emitting layer is the organometallic complex of the present invention.

[0090] More preferably, the doping concentration of the organometallic complex in the host material is 3-20%, more preferably 5-17%, and even more preferably 8-14%. Device performance is optimal when the doping concentration of the organometallic complex in the host material is approximately 10%. The doping concentration is expressed as a mass percentage.

[0091] In a fourth aspect, the present invention provides a display device comprising the organic electroluminescent device.

[0092] In a fifth aspect, the present invention provides a lighting device comprising the organic electroluminescent device. DETAILED DESCRIPTION

[0093] The technical solutions of the present invention are described in detail below through specific examples. The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention. Any other equivalent changes or modifications that do not depart from the spirit disclosed by the present invention should be included in the scope of the claims.

[0094] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0095] The materials and structures described in this invention can also be used in other organic electronic devices listed above.

[0096] Definition of Substituent Terms

[0097] In the present invention, the expression of chemical elements, unless otherwise specified, includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (hydrogen), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C. 13 C, etc.

[0098] In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatom of the heterocycloalkyl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatom of the alicyclic heterocycle is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0099] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0100] In the present invention, "——*" and "*" both represent the connection site of a group.

[0101] In the present invention, “each independently” means that when there are multiple subjects, they may be the same or different.

[0102] In the present invention, the expression Ca-Cb represents that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.

[0103] In the present invention, 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.

[0104] In the present invention, the C3-C20 can be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0105] In the present invention, the C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0106] In the present invention, the C6-C30 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0107] In the present invention, the C3-C30 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0108] In the present invention, unless otherwise specified, the C6-C30 aryl group (C6-C30 aromatic ring) includes a monocyclic aryl group and a condensed ring aryl group; the monocyclic aryl group means a group containing at least one phenyl group, and when containing at least two phenyl groups, the phenyl groups are connected by a single bond, including but not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the condensed ring aryl group means a group containing at least two rings (and at least one ring is an aromatic ring), and the rings share two adjacent carbon atoms and are condensed to each other, for example The fluorenyl radical includes, but is not limited to, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl, benzofluorenyl (benzo[A]fluorenyl, benzo[B]fluorenyl, benzo[C]fluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene, It should be noted that monocyclic aromatic groups and condensed aromatic groups connected by a single bond also fall within the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, binaphthyl, etc.

[0109] In the present invention, the C6-C30 heteroaryl group (C3-C30 heteroaromatic ring) includes a monocyclic heteroaryl group or a condensed-ring 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 aryl, heteroaryl, etc.), the heteroaryl group and the other group are connected by a single bond, and illustratively include but are not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused ring heteroaryl group refers to a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two groups share two adjacent atoms fused to each other, including but not limited to: quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, benzonaphthofuranyl (benzo[B]naphtho[2,3-D]furanyl, benzo[B]naphtho[1,2-D] [B] naphtho[2,1-D]thiophenyl), carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc.

[0110] In the present invention, specific examples of the C6-C30 arylamino group are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above-mentioned aryl group, including but not limited to phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrenylamino, biphenylamino, etc. Specific examples of the C3-C30 heteroarylamino group are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above-mentioned heteroaryl group, including but not limited to pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0111] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting any of the above-mentioned aryl groups with O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting any of the above-mentioned heteroaryl groups with O. The C6-C30 arylthio group is a monovalent group formed by connecting any of the above-mentioned aryl groups with S, and the C3-C30 heteroarylthio group is a monovalent group formed by connecting any of the above-mentioned heteroaryl groups with S.

[0112] In the present invention, the C3-C10 alicyclic ring, preferably the C4-C10 alicyclic ring, includes a saturated alicyclic ring or an unsaturated alicyclic ring, preferably a saturated alicyclic ring. The C2-C10 heterocyclic ring, preferably the C3-C10 heterocyclic ring, includes a saturated alicyclic ring or an unsaturated alicyclic ring, preferably a saturated alicyclic ring, which can be understood as a ring structure formed by replacing at least one ring carbon atom in the alicyclic ring with a heteroatom (such as N, S, O, etc.).

[0113] In the present invention, the C1-C20 alkyl group is preferably a C1-C16 alkyl group, and further preferably a C1-C10 alkyl group, which illustratively 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.

[0114] In the present invention, specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned alkyl groups to O.

[0115] In the present invention, a specific example of the C1-C20 alkylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned alkyl group, including but not limited to: trimethylsilyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, triethylsilyl, tripropylsilyl, etc.

[0116] In the present invention, the C3-C20 cycloalkyl group, preferably a C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. A monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and a polycyclic alkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more ring carbon atoms, including but not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl groups.

[0117] In the present invention, specific examples of the C2-C20 heterocycloalkyl group include groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), including but not limited to: epoxy, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrrolyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxane, morpholinyl, etc.

[0118] In the present invention, the C2-C20 alkenyl group, preferably the C2-C10 alkenyl group, contains at least one C=C, and illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0119] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered equivalent.

[0120] In the compounds described herein, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms, such as carbon and nitrogen, may also be replaced by their other stable isotopes. The replacement of compounds with other stable isotopes may be preferred because it enhances device efficiency and stability.

[0121] In the compounds described herein, multiple substitution refers to a range including disubstitution up to the maximum number of available substitutions. When a substituent in a compound described herein represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on the structure, and the substituents present at multiple available substitution positions can have the same structure or different structures.

[0122] In the present invention, "combination" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by a person skilled in the art from the applicable list. For example, an alkyl group and a deuterium group are combined to form a partially or fully deuterated alkyl group (e.g., a deuterated methyl group, a deuterated tert-butyl group); a halogen group and an alkyl group are combined to form a partially or fully halogenated alkyl group (e.g., a trifluoromethyl group); or a halogen group, an alkyl group, and an aryl group are combined to form a halogenated arylalkyl group, etc.

[0123] In the compounds mentioned in the present invention, unless explicitly limited, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present invention, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the ring formed can be a monocyclic or polycyclic ring, as well as an alicyclic, alicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0124] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more equipment conventional in the art (including but not limited to Agilent's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, fluorescence spectrophotometer, electrochemical workstation, sublimator, etc.), and has been tested for structure confirmation and characteristics by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested using equipment conventional in the art (including but not limited to the vapor deposition machine produced by Nanjing Institute of Microbiology, the optical testing system and life test system produced by Suzhou Fushida, the ellipsometer produced by Wuhan Yiguang Technology, etc.), and have been tested by methods well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the testing method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned relevant contents are no longer expanded and repeated in the present invention.

[0125] The preparation method of the compound of the present invention is not limited. The following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0126] Example 1, Synthesis of Compound I-56:

[0127]

[0128] (1-1) Synthesis of intermediate S1-1:

[0129] Under nitrogen protection, raw material M1-1 (86.04 g), raw material M1-2 (115.48 g), anhydrous potassium carbonate (138.21 g), Pd(PPh3)4 (11.56 g), toluene (600 mL), ethanol (200 mL) and deionized water (100 mL) were added to a dry three-necked reaction flask, and the temperature was slowly raised to 100°C with stirring for 5 hours. After the reaction was completed, the temperature was cooled to room temperature, and toluene (200 mL) was added for extraction. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain intermediate S1-1 (109.23 g, yield 78.3%).

[0130] (1-2) Synthesis of intermediate S1-2:

[0131] Under nitrogen, intermediate S1-1 (83.73 g), triphenylphosphine (196.71 g), and o-dichlorobenzene (450 mL) were added to a dry three-necked reaction flask. The temperature was raised to 130°C with stirring and the reaction was allowed to proceed for 32 h. After the reaction, the mixture was cooled to room temperature, filtered, evaporated under reduced pressure, and purified by column chromatography to obtain intermediate S1-2 (62.42 g, 84.2% yield).

[0132] (1-3) Synthesis of intermediate S1-3:

[0133] Under nitrogen, to a dry three-necked reaction flask were added intermediate S1-2 (49.42 g), raw material M1-3 (31.39 g), sodium tert-butoxide (38.44 g), Pd2(dba)3 (3.66 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (7.63 g), and toluene (500 mL). The temperature was slowly raised to 105°C with stirring and the reaction was allowed to proceed for 4 h. After cooling, the reaction solution was added with water (200 mL), washed with water, concentrated, purified by column chromatography, recrystallized, and dried to obtain intermediate S1-3 (46.78 g, 72.2% yield).

[0134] (1-4) Synthesis of intermediate S1-4:

[0135] Under nitrogen, intermediate S1-3 (32.41 g) and dichloromethane (200 mL) were added to a dry three-necked reaction flask. The mixture was cooled to 0°C with stirring, and boron tribromide (30 mL) was added dropwise. The reaction was allowed to react for 1 h. The reaction was quenched with water (100 mL), and dichloromethane (300 mL) was added for extraction. The organic phase was dried and purified by column chromatography to obtain intermediate S1-4 (26.59 g, 85.7% yield).

[0136] (1-5) Synthesis of intermediate S1-5:

[0137] Under nitrogen, to a dry three-necked reaction flask were added intermediate S1-4 (24.81 g), raw material M1-4 (35.72 g), tripotassium phosphate (33.96 g), cuprous iodide (1.52 g), 2-picolinic acid (0.98 g), and DMSO (400 mL). The mixture was heated to 160°C with stirring and reacted for 14 h. After the reaction, the temperature was cooled to room temperature and extracted with ethyl acetate (300 mL). The organic phase was collected, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate S1-5 (33.63 g, 67.0% yield).

[0138] (1-6) Synthesis of intermediate S1-6:

[0139] Under nitrogen, to a dry three-necked reaction flask were added intermediate S1-5 (31.35 g), raw material M1-5 (14.81 g), sodium tert-butoxide (9.16 g), Pd2(dba)3 (0.92 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.91 g), and toluene (350 mL). The temperature was slowly raised to 105°C with stirring and the reaction was allowed to proceed for 4 h. After the reaction, the temperature was cooled to room temperature, water (200 mL) was added, the mixture was washed with water, concentrated, purified by column chromatography, recrystallized, and dried to obtain intermediate S1-6 (30.07 g, 71.3% yield).

[0140] (1-7) Synthesis of intermediate S1-7:

[0141] Under nitrogen, intermediate S1-6 (16.87 g), ammonium hexafluorophosphate (6.52 g), and triethyl orthoformate (100 mL) were added to a dry three-necked reaction flask and heated to 80°C for 2.5 h. After the reaction, the temperature was cooled to room temperature, and water (200 mL) and ethyl acetate (200 mL) were added for extraction. The combined organic phases were spin-dried and purified by column chromatography to obtain intermediate S1-7 (15.67 g, 78.4% yield).

[0142] (1-8) Synthesis of compound I-56:

[0143] Under nitrogen, intermediate S1-7 (9.99 g), (1,5-cyclooctadiene)platinum dichloride (4.12 g), sodium acetate (1.64 g), and dioxane (180 mL) were added to a dry three-necked reaction flask and stirred at 110°C for 72 h. After the reaction, the temperature was cooled to room temperature and extracted with ethyl acetate (300 mL). The organic phase was collected, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain compound I-56 (2.80 g, 26.8% yield).

[0144] MS (m / e) of compound I-56: 1046.48; 1 HNMR (400MHz, DMSO-d6): δ8.49-8.40(m,2H),8.13-7.99(m,5H),7.95-7.88(m,2H),7.79(d,1H),7.67-7.6 1(m,2H),7.58-7.47(m,2H),7.40-7.34(m,2H),7.31-6.98(m,8H),6.92(d,2H),6.70(d,1H),1.35(s,18H).

[0145] Example 2, Synthesis of Compound I-65:

[0146]

[0147] The synthetic route of compound I-65 is the same as that of compound I-56, and compound I-65 can be obtained by simply replacing raw material M1-5 with raw material M2-1.

[0148] MS (m / e) of compound I-65: 1096.21; 1HNMR (400MHz, DMSO-d6): δ8.49-8.40(m,2H),8.13-7.99(m,5H),7.95-7.88(m,2H),7.79(d,1 H),7.67-7.61(m,2H),7.56-7.49(m,2H),7.43-7.33(m,5H),7.31-7.00(m,7H),6.74(d,1H).

[0149] Example 3, Synthesis of Compound I-77:

[0150]

[0151] The synthetic route of compound I-77 is the same as that of compound I-56. Compound I-77 can be obtained by replacing raw material M1-3 with raw material M3-1 and raw material M1-5 with raw material M3-2.

[0152] MS (m / e) of compound I-77: 1061.76; 1 HNMR (400MHz, DMSO-d6): δ8.94(d,1H),8.87(d,1H),8.65(dd,1H),8.49-8.41(m,1H),8.32(d,1H),8.21(dd, 1H),8.10-7.99(m,5H),7.92(d,1H),7.86-7.76(m,4H),7.67-7.61(m,2H),7.57-6.98(m,15H),6.70(d,1H).

[0153] Example 4, Synthesis of Compound I-90:

[0154]

[0155] (4-1) Synthesis of raw material M4-3c:

[0156] Under nitrogen, to a dry three-necked reaction flask were added raw material M4-3a (26.61 g), raw material M4-3b (13.80 g), sodium tert-butoxide (19.22 g), Pd2(dba)3 (1.83 g), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (3.81 g), and toluene (200 mL). The temperature was slowly raised to 105°C with stirring and the reaction was allowed to proceed for 4 h. After the reaction, the temperature was lowered to room temperature, water (200 mL) was added, the product was washed with water, concentrated, purified by column chromatography, recrystallized, and dried to obtain raw material M4-3c (24.48 g, 75.5% yield).

[0157] (4-2) Synthesis of raw material M4-3:

[0158] Under nitrogen, a dry, three-necked reaction flask was charged with raw material M4-3c (22.69 g), tin (29.08 g), HCl solution (40.25 g, 35 wt%), and ethanol (500 mL). The mixture was heated to 85°C with stirring and reacted for 14 h. After the reaction, the mixture was cooled to room temperature and washed with saturated sodium bicarbonate solution until neutral. Ethyl acetate (500 mL) was added for extraction, followed by washing with saturated sodium chloride solution, drying over anhydrous sodium sulfate, and purification by column chromatography to obtain raw material M4-3 (15.07 g, 73.2% yield).

[0159] (4-3) Synthesis of Compound I-90:

[0160] The synthetic route of compound I-90 is the same as that of compound I-56. Compound I-90 can be obtained by replacing raw material M1-1 with raw material M4-2, raw material M1-2 with raw material M4-1, and raw material M1-5 with raw material M4-3.

[0161] MS (m / e) of compound I-90: 1056.74; 1 HNMR (400MHz, DMSO-d6): δ8.43(dd,1H),8.14-8.03(m,3H),7.98-7.89(m,2H),7.73-7.61(m,3H),7.57(s,1H),7.48(t,1H),7.41-6.9 8(m,11H),6.91-6.82(m,2H),6.72(d,1H),4.03(s,1H),3.98(s,1H),1.84-1.73(m,2H),1.68-1.57(m,2H),1.33(d,6H),1.28(d,6H).

[0162] Example 5, Synthesis of Compound I-122:

[0163]

[0164] The synthetic route of compound I-122 is the same as that of compound I-56. Compound I-122 can be obtained by replacing raw material M1-1 with raw material M5-1 and raw material M1-5 with raw material M5-2.

[0165] MS (m / e) of compound I-122: 1072.11; 1HNMR (400MHz, DMSO-d6): δ8.43(dd,1H),8.19(dd,1H),8.10-8.03(m,2H),8.00-7.89(m,3H) ,7.68-7.61(m,2H),7.48-7.34(m,4H),7.31-6.91(m,12H),6.72(d,1H),1.44-1.38(m,21H).

[0166] Example 6, Synthesis of Compound I-129:

[0167]

[0168]

[0169] (6-1) Synthesis of raw material M6-1:

[0170] The synthetic route of raw material M6-1 is the same as that of raw material M4-3. Raw material M6-1 can be obtained by replacing raw material M4-3a with raw material M6-1a. (6-2) Synthesis of compound I-129:

[0171] The synthetic route of compound I-129 is the same as that of compound I-122, and compound I-129 can be obtained by simply replacing raw material M5-2 with raw material M6-1.

[0172] MS (m / e) of compound I-129: 1254.47; 1 HNMR (400MHz, DMSO-d6): δ8.43(dd,1H),8.19(dd,1H),8.10-8.03(m,2H),8.00-7.81( m,7H),7.67-7.61(m,2H),7.48-6.97(m,20H),6.84-6.68(m,4H),1.44-1.35(m,12H).

[0173] Example 7, Synthesis of Compound I-142:

[0174]

[0175] The synthetic route of compound I-142 is the same as that of compound I-90, except that raw material M4-1 is replaced by raw material M7-1, and raw material M4-3 is replaced by raw material M7-2 to obtain compound I-142.

[0176] MS (m / e) of compound I-142: 967.58; 1HNMR (400MHz, DMSO-d6): δ8.43(dd,1H),8.10-8.03(m,3H),7.95-7.89(m,2H),7.73(dd,1H),7 .67-7.61(m,2H),7.54(s,1H),7.47-7.34(m,3H),7.32-7.02(m,8H),6.76(d,1H),5.35(d,2H).

[0177] Example 8, Synthesis of Compound I-166:

[0178]

[0179]

[0180] (8-1) Synthesis of raw material M8-1:

[0181] The synthetic route of raw material M8-1 is the same as that of raw material M4-3. Raw material M8-1 can be obtained by replacing raw material M4-3a with raw material M8-1a and raw material M4-3b with raw material M8-1b.

[0182] (8-2) Synthesis of Compound I-166:

[0183] The synthetic route of compound I-166 is the same as that of compound I-122. Compound I-166 can be obtained by simply replacing raw material M5-2 with raw material M8-1.

[0184] MS (m / e) of compound I-166: 1182.91; 1 HNMR (400MHz, DMSO-d6): δ8.43(dd,1H),8.19(dd,1H),8.10-7.89(m,7H),7.70-7.53(m,8H),7.51 -7.34(m,9H),7.31-7.19(m,3H),7.17-7.11(m,2H),7.06(s,1H),6.72(d,1H),1.44-1.34(m,12H).

[0185] Example 9, Synthesis of Compound I-183:

[0186]

[0187] The synthetic route of compound I-183 is the same as that of compound I-122. Compound I-183 can be obtained by replacing raw material M5-1 with raw material M9-1, raw material M1-3 with raw material M9-2, and raw material M5-2 with raw material M9-3.

[0188] MS (m / e) of compound I-183: 1190.27; 1 HNMR (400MHz, DMSO-d6): δ8.99(d,1H),8.10-8.03(m,2H),8.00-7.92(m,2H),7.89-7.80(m,2H),7.72-7.61(m,3H),7.58-7.5 0(m,2H),7.48-7.24(m,15H),7.21-7.06(m,4H),7.05-6.97(m,5H),6.94-6.88(m,2H),6.72(d,1H),1.54(s,3H),1.49(s,3H).

[0189] Example 10, Synthesis of Compound I-216:

[0190]

[0191]

[0192] (10-1) Synthesis of raw material M10-2:

[0193] The synthetic route of raw material M10-2 is the same as that of raw material M4-3. Raw material M10-2 can be obtained by replacing raw material M4-3a with raw material M10-2a. (10-2) Synthesis of raw material M10-1a:

[0194] Under nitrogen, naphthalene (25.61 g) and dichloroethane (200 mL) were added to a dry three-necked reaction flask, stirred and cooled to 0°C to -10°C, anhydrous aluminum chloride (34.71 g) was added, and a solution of methyl 3-bromo-3-methylbutyrate (38.81 g) in dichloroethane (40 mL) was added dropwise at 0°C to -10°C. The mixture was incubated for 0.5 h, allowed to warm to room temperature, and stirred for 2 h. After the reaction, the mixture was poured into ice water (500 mL), allowed to stand and separate, and the organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride solutions until neutral, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under vacuum to dryness. The crystals were dissolved in ethanol (100 mL) and filtered to obtain raw material M10-1a (42.32 g, yield 87.7%).

[0195] (10-3) Synthesis of raw material M10-1b:

[0196] Under nitrogen, tetrahydrofuran (200 mL) and raw material M10-1a (24.21 g) were added to a dry three-necked reaction flask. The mixture was stirred and cooled to -10°C to -5°C. A solution of methylmagnesium chloride (15.71 g) in tetrahydrofuran (100 mL) was added dropwise over a period of approximately 1 hour. The mixture was then kept at 0°C to -5°C for 1 hour, and then naturally heated to room temperature with stirring for 8 hours. Concentrated hydrochloric acid (100 mL) was added dropwise below 0°C, stirred for 5 minutes, and ethyl acetate (500 mL) was added. The mixture was allowed to stand and separate. The organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride solutions until neutral. The solvent was evaporated under vacuum to obtain raw material M10-1b (20.19 g, 83.4% yield). (10-4) Synthesis of raw material M10-1c:

[0197] Under nitrogen, raw material M10-1b (19.37 g), glacial acetic acid (100 mL), and concentrated hydrochloric acid (10 mL) were added to a dry three-necked reaction flask, stirred, and heated to 100°C for 4 h. After completion of the reaction, the temperature was lowered to room temperature, poured into ice water (300 mL), and extracted with dichloromethane (300 mL). The organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride solutions until neutral. The solvent was evaporated to dryness under normal pressure, and the residue was dissolved in anhydrous ethanol (40 mL) and toluene (20 mL) to crystallize. The solid was filtered and dried to obtain raw material M10-1c (12.12 g, 67.6% yield).

[0198] (10-5) Synthesis of raw material M10-1:

[0199] Under nitrogen, raw material M10-1c (11.21 g) and dichloromethane (100 mL) were added to a dry three-necked reaction flask and stirred at room temperature for 30 min. N-bromosuccinimide (NBS, 8.90 g) was then added and stirred overnight to complete the reaction. After the reaction, the mixture was washed three times with water (200 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain raw material M10-1 (10.97 g, 72.6% yield).

[0200] (10-6) Synthesis of compound I-216:

[0201] The synthetic route of compound I-216 is the same as that of compound I-90, except that raw material M4-1 is replaced by raw material M10-1, and raw material M4-3 is replaced by raw material M10-2 to obtain compound I-216.

[0202] MS (m / e) of compound I-216: 1136.42; 1HNMR (400MHz, DMSO-d6): δ8.43(dd,1H),8.22-8.15(m,2H),8.10-8.03(m,2H),8.00-7.88(m,4H),7.84(dd,1H),7.70-7.64(m,3H) ,7.58(s,1H),7.52-7.43(m,3H),7.41-7.34(m,2H),7.31-6.97(m,9H),6.72(d,1H),2.13(s,1H),1.97(s,1H),1.41-1.30(m,12H).

[0203] Example 11, Synthesis of Compound I-225:

[0204]

[0205] (11-1) Synthesis of raw material M11-2:

[0206] The synthetic route of raw material M11-2 is the same as that of raw material M4-3. Raw material M11-2 can be obtained by replacing raw material M4-3a with raw material M11-2a. (11-2) Synthesis of compound I-225:

[0207] The synthetic route of compound I-225 is the same as that of compound I-90, except that raw material M4-1 is replaced by raw material M11-1, and raw material M4-3 is replaced by raw material M11-2 to obtain compound I-225.

[0208] MS (m / e) of compound I-225: 1032.71; 1 HNMR (400MHz, DMSO-d6): δ8.43(dd,1H),8.10-8.03(m,3H),7.95-7.88(m,2H),7.67-7.61(m,2H),7.50-7.43(m,2H),7. 41-7.34(m,2H),7.31-6.91(m,10H),6.87-6.81(m,2H),6.72(d,1H),6.18(d,2H),2.80-2.69(m,4H),1.79-1.67(m,4H).

[0209] The present invention exemplifies the specific synthesis methods of the above compounds. For other compounds for which no specific synthesis methods are given, they can be prepared by similar methods by simply replacing the raw materials. They will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0210] Device Example 1

[0211] The preparation method of the organic electroluminescent device is as follows:

[0212] (1) A glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio 1:1), baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0213] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -3 Pa, vacuum evaporating HIL on the above-mentioned anode layer film as a hole injection layer, the HIL includes a hole transport material HT01 and a P-type dopant material HI, with a doping mass percentage concentration of 2%, forming a hole injection layer of the device, the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 10nm; then evaporating the hole transport layer HT01 at a evaporation rate of 0.1nm / s and a thickness of 60nm; then evaporating the electron blocking layer EB at a evaporation rate of 0.1nm / s and a evaporation film thickness of 5nm;

[0214] (3) Vacuum evaporating an EML on the electron blocking layer as the light-emitting layer of the device, wherein the EML comprises the main materials BH1, BH2 and the compound I-56 (phosphorescent dye) of the present invention, the evaporation mass ratio of BH1 and BH2 is 5:5, the doping mass percentage concentration of the compound I-56 is 10%, and the organic light-emitting layer of the device is formed at a evaporation rate of 0.2 nm / s and a total evaporation film thickness of 30 nm;

[0215] (4) Evaporating ET01:LiQ with a mass ratio of 1:1 on the light-emitting layer as the electron transport material of the device electron transport layer at a evaporation rate of 0.1 nm / s and a total film thickness of 30 nm;

[0216] (5) LiQ with a thickness of 1 nm was vacuum evaporated on the electron transport layer as the electron injection layer, and an Al layer with a thickness of 150 nm was used as the cathode of the device.

[0217] Device Examples 2-11, Device Comparative Example 1

[0218] The only difference between it and device embodiment 1 is that the phosphorescent dyes of the light-emitting layer are the compounds shown in Table 1; other layers, thicknesses, materials and preparation methods are the same as those of device embodiment 1.

[0219] The molecular structure of each functional layer material is as follows:

[0220]

[0221] Table 1 lists the current density of 10mA / cm2 Under these conditions, the maximum emission wavelength (λ max , nm), external quantum efficiency (EQE, %) and lifetime (LT 95 , h). In Table 1, the EQE and LT of the device comparative example 1 are shown in FIG. 95 The test value of life is recorded as 1.00, and the EQE and LT of other devices are 95 The lifespans are the ratios of their respective test values to the test values of device comparative example 1 (relative EQE, relative lifespan).

[0222] Table 1

[0223] Device Phosphorescent dyes <![CDATA[λ max (nm)]]> Relative EQE Relative lifespan Device Example 1 I-56 460 1.14 1.18 Device Example 2 I-65 461 1.14 1.20 Device Example 3 I-77 462 1.15 1.19 Device Example 4 I-90 461 1.16 1.21 Device Example 5 I-122 459 1.21 1.27 Device Example 6 I-129 459 1.20 1.28 Device Example 7 I-142 463 1.18 1.24 Device Example 8 I-166 463 1.21 1.21 Device Example 9 I-183 461 1.20 1.27 Device Example 10 I-216 461 1.22 1.26 Device Example 11 I-225 464 1.17 1.23 Device Comparative Example 1 D-1 490 1.00 1.00

[0224] As can be seen from Table 1, compared with the device formed by the compound used in Device Comparative Example 1, the external quantum efficiency EQE of the devices formed by the compounds used in Device Examples 1-11 is improved (up to 22%), and the lifetime is improved by at least 18%.

[0225] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments of the present invention. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be restrictive.

Claims

1. An organometallic complex having a structure represented by formula (I): In formula (I), M is selected from metals with a relative atomic mass greater than 40; Q1-Q3 are each independently selected from C or N; L is selected from a single bond, O, S, S=O, SO2, Se, Se=O, SeO2, SiR L1 R L2 NR L3 , CR L4 R L5 、C=O、GeR L6 R L7 PR L8 、 R L9 P=O、BR L10 Any of the following; A1-A8 are each independently selected from CR A or N; Z1-Z8 are each independently selected from CR Z or N; M1-M8 are each independently selected from CR M or N; R N 、R L1 -R L10 、R A 、R Z 、R M are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, ester, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, 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, substituted or unsubstituted C6-C30 arylthio, and substituted or unsubstituted C3-C30 heteroarylthio; said R N 、R L1 -R L10 、R A 、R Z 、R M Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds; The R N 、R L1 -R L10 、R A 、R Z 、R M The substituents substituted in the alkyl group are each independently selected from any one of deuterium, halogen, cyano, nitro, hydroxyl, ester, amino, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, and C3-C30 heteroarylthio; and the substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

2. The organometallic complex according to claim 1, characterized in that At most two of A1, A2, A3, and A4 are selected from N; and / or at most two of A5, A6, A7, and A8 are selected from N; Preferably, one of A1, A2, A3, A4 is selected from N; and / or one of A5, A6, A7, A8 is selected from N; or A1, A2, A3, A4, A5, A6, A7, A8 are each independently selected from CR A .

3. The organometallic complex according to claim 1 or 2, characterized in that Each of the RA groups is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 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, substituted or unsubstituted C6-C30 arylthio, and substituted or unsubstituted C3-C30 heteroarylthio; and R A Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds; Preferably, the R A Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 arylamino, and substituted or unsubstituted C3-C20 heteroarylamino; Preferably, the substituents substituted in RA are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, the R A The substituents substituted in are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; Preferably, the R A Each is independently selected from hydrogen, deuterium, halogen, cyano, or any of the following groups which may be substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, isopentyl, tert-pentyl, neopentyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl, tetrahydrothiopyranyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, 2,3-dihydroindanyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, pyridyl, furanyl, benzofuranyl, dibenzofuranyl, benzonaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, benzonaphthothienyl, carbazolyl, N-phenylcarbazolyl, Ar1 and Ar2 are each independently selected from any one of phenyl, naphthyl, pyridyl, dibenzofuranyl and dibenzothiophenyl; Preferably, the R A The substituted substituents are each independently selected from any one or a combination of two of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, and pyridyl.

4. The organometallic complex according to claim 1, characterized in that At most one of Z1, Z2, Z3, and Z4 is selected from N; and / or at most one of Z5, Z6, Z7, and Z8 is selected from N; Preferably, Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are each independently selected from CR Z ; Preferably, the R Z Each is independently selected from any one or a combination of at least two of hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C6-C20 aryl, and C3-C20 heteroaryl; the R Z Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds; Preferably, the R Z Each is independently selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, methyl, tert-butyl, phenyl, naphthyl, and pyridyl. More preferably, the R Z are all selected from hydrogen.

5. The organometallic complex according to claim 1, characterized in that At most one of M1 and M2 is selected from N; and / or at most one of M3, M4, M5, and M6 is selected from N; and / or at most one of M7 and M8 is selected from N; Preferably, M1, M2, M3, M4, M5, M6, M7, and M8 are each independently selected from CR M ; Preferably, M1, M2, M3, M4, M5, and M8 are selected from CH, and M6 and M7 are each independently selected from CR M .

6. The organometallic complex according to claim 1 or 5, characterized in that The R M Each is independently selected from any one or a combination of at least two of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; the R M Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds; Preferably, the R M Each is independently selected from any one or a combination of two of hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, and pyridyl; Preferably, R in M6 M and R in M7 M They are not connected or connected by chemical bonds to form substituted or unsubstituted C4-C10 alicyclic rings, or substituted or unsubstituted C3-C10 heterocyclic rings; Preferably, the substituents in the above-mentioned ring "substituted or unsubstituted" are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl.

7. The organometallic complex according to any one of claims 1 to 6, characterized in that RN is selected from any one of deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, wherein R N Not connected to adjacent groups or connected to form a ring through chemical bonds; Preferably, the R N The substituents substituted in the substituted are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, the RN is selected from any one of deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and the R N Not connected to adjacent groups or connected to form a ring through chemical bonds; Preferably, the RN is selected from any one of deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; Preferably, the R N The substituents substituted in are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, the R N The substituents substituted in are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C2-C8 heterocycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl; Preferably, the R N deuterium, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, isopentyl, tert-pentyl, neopentyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl, tetrahydrothiopyranyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, 2,3-dihydroindenyl, 1,2,3,4-tetrahydronaphthyl, naphthyl, naphthylphenyl, phenylnaphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, fluorenyl, spirofluorenyl, benzofluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, bipyridyl, furyl, benzofuranyl, dibenzofuranyl, benzonaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, benzonaphthothienyl, N-phenylcarbazolyl; Preferably, the R N The substituents substituted in the above-mentioned group are each independently selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, isobutyl, sec-butyl, isopentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, 2,3-dihydroindanyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, and carbazolyl, or a combination of any one or two thereof.

8. The organometallic complex according to any one of claims 1 to 7, characterized in that The L is selected from a single bond, O, S, Se, SiR L1 R L2 NR L3 , CR L4 R L5 BR L10 Any of the following; Among them, R L1 、R L2 、R L3 、R L4 、R L5 、R L10 Each is independently selected from any one or a combination of at least two of C1-C6 alkyl, C3-C8 cycloalkyl, C2-C8 heterocycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl, wherein R L1 、R L2 、R L3 、R L4 、R L5 、R L10 Each independently is not connected to the adjacent group or is connected to form a ring through a chemical bond; preferably, the L is selected from a single bond, O, S, SiR L1 R L2 NR L3 , CR L4 R L5 ; More preferably, said L is selected from a single bond, O, S; further, said L is selected from O; and / or, The M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir or Pt; preferably, the M is selected from Pt or Pd; more preferably, the M is selected from Pt; And / or, Q1 is selected from N, Q2, and Q3 are both selected from C.

9. The organometallic complex according to claim 1, characterized in that The organometallic complex has a structure shown in formula (II-1) or formula (II-2): In formula (II-1) and formula (II-2), M, L, and R N Having the same definition as in formula (I), R A1 、R A2 、R Z1 、R Z2 、R M1 、R M2 、R M2’ Each independently represents no substitution, monosubstitution to the maximum permissible substitution; The R A1 、R A2 、R Z1 、R Z2 、R M1 、R M2 、R M2’ are each independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, 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, substituted or unsubstituted C6-C30 arylthio, and substituted or unsubstituted C3-C30 heteroarylthio; said R A1 、R A2 、R Z1 、R Z2 、R M1 、R M2 、R M2’ Each independently is not connected to the adjacent groups or is connected to form a ring through chemical bonds; The R A1 、R A2 、R Z1 、R Z2 、R M1 、R M2 、R M2’ The substituents substituted in the alkyl group are each independently selected from any one of deuterium, halogen, cyano, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, and C3-C30 heteroarylthio, or a combination of at least two thereof; the substituents are each independently not connected to adjacent ring structures or are connected to form a ring by chemical bonds; In formula (II-2), ring A is selected from a substituted or unsubstituted C4-C10 alicyclic ring, or a substituted or unsubstituted C3-C10 alicyclic heterocyclic ring; wherein the substituents substituted in the ring A are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl; Preferably, ring A is selected from Any one of the following, the dotted line represents a fused bond; wherein, the ring A is optionally substituted by any one or at least two substituents selected from deuterium, halogen, cyano, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, and pyridyl.

10. The organometallic complex according to claim 1, characterized in that The organometallic complex is selected from the group consisting of the following compounds:

11. Use of the organometallic complex according to any one of claims 1 to 10 in the preparation of an organic electronic device, preferably the organic electronic device is an organic electroluminescent device, preferably as a phosphorescent dye.

12. An organic electroluminescent device comprising a substrate and an anode layer, one or more light-emitting unit layers, and a cathode layer sequentially formed on the substrate; the one or more light-emitting unit layers comprise a light-emitting layer, and the phosphorescent dye in the light-emitting layer comprises the organic metal complex according to any one of claims 1 to 10.

13. A display device or lighting device comprising the organic electroluminescent device according to claim 12.

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