Organic luminescent material containing 6-silyl-substituted isoquinoline ligand

1. A metal complex, having a general formula of M(L a ) m (L b ) n (L c ) q , wherein L a , L b and L c are a first ligand, a second ligand and a third ligand coordinated to the metal M respectively;

wherein L a , L b and L c may be optionally joined to form a multidentate ligand;

wherein m is 1 or 2, n is 1 or 2, q is 0 or 1, and m+n+q equals to the oxidation state of the metal M;

when m is greater than 1, the L a may be the same or different; and when n is greater than 1, the L b may be the same or different;

wherein the first ligand L a is represented by Formula 1:

wherein,

R 1 to R 3 are each independently selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof;

X 1 to X 4 are each independently selected from CR 4 or N;

wherein R 4 is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

in Formula 1, adjacent substituents can be optionally joined to form a ring;

hydrogen in the ligand L a can be optionally partially or fully substituted by deuterium;

wherein L b has a structure represented by Formula 2:

wherein R t to R z are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

in Formula 2, for substituents R x , R y , R z , R t , R u , R v and R w , adjacent substituents can be optionally joined to form a ring; and

wherein L c is a monoanionic bidentate ligand.

2. The metal complex of claim 1 , wherein the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt.

3. The metal complex of claim 1 , wherein X 1 to X 4 are each independently selected from CR 4 , and R 4 is independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group and a phosphino group, and combinations thereof.

4. The metal complex of claim 1 , wherein X 1 and/or X 3 are(is) each independently selected from CR 4 , and R 4 is independently selected from hydrogen, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or combinations thereof.

5. The metal complex of claim 1 , wherein R 1 , R 2 and R 3 are each independently selected from the group consisting of: methyl, ethyl, n-propyl, isopropyl, isobutyl, t-butyl, isopentyl, neopentyl, phenyl, pyridyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated isobutyl, deuterated t-butyl, deuterated isopentyl, deuterated neopentyl, deuterated phenyl, deuterated pyridyl, deuterated cyclopropyl, deuterated cyclobutyl, deuterated cyclopentyl, deuterated cyclohexyl, and combinations thereof.

6. The metal complex of claim 1 , wherein R 1 , R 2 and R 3 are each independently selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms.

7. The metal complex of claim 1 , wherein L a has any one structure or any two structures selected from the group consisting of L a1 to L a693 :

8. The metal complex of claim 1 , wherein in Formula 2, R t to R z are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.

9. The metal complex of claim 1 , wherein L b has any one structure or any two structures independently selected from the group consisting of L b1 to L b365 :

10. The metal complex of claim 1 , wherein L c has any one structure selected from:

wherein R a , R b and R c may represent mono-substitution, multi-substitution or non-substitution;

X b is selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

R a , R b , R c , R N1 , R C1 and R C2 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group and a phosphino group, and combinations thereof;

in the structure of L c , adjacent substituents can be optionally joined to form a ring.

11. The metal complex of claim 1 , wherein the ligand L c is any one selected from the group consisting of L c1 to L c99 :

12. The metal complex of claim 7 , wherein hydrogen in the ligands L a may be partially or fully substituted by deuterium.

13. The metal complex of claim 9 , wherein hydrogen in the ligands L b may be partially or fully substituted by deuterium.

14. The metal complex of claim 7 , wherein the metal complex is Ir(L a ) 2 (L b ), and L a is any one or two selected from L a1 to L a693 , and optionally, hydrogen in the ligands L a and L b may be partially or fully substituted by deuterium,

wherein L b has any one structure or any two structures independently selected from the group consisting of L b1 to L b365 :

15. The metal complex of claim 7 , wherein the metal complex is Ir(L a )(L b )(L c ), and L a is any one selected from L a1 to L a693 , and optionally, hydrogen in the ligands L a and L b may be partially or fully substituted by deuterium

wherein L b has any one structure or any two structures independently selected from the group consisting of L b1 to L b365 :

the ligand L c is any one selected from the group consisting of L c1 to L c99 :

16. The metal complex of claim 1 , wherein the metal complex is selected from the group consisting of

17. An electroluminescent device, comprising:

an anode,

a cathode, and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex of claim 1 .

18. The device of claim 17 , wherein the organic layer is a light-emitting layer, and the metal complex is a light-emitting material; the organic layer further comprises a host material; the host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, aza-dibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene and azaphenanthrene, and combinations thereof.

19. The device of claim 17 , wherein the device emits red light or white light.

20. A compound formulation, comprising the metal complex of claim 1 .

21. The metal complex of claim 3 , wherein R 4 is independently selected from the group consisting of: hydrogen, fluorine, methyl, ethyl, isopropyl, t-butyl, cyclopentyl, cyclohexyl, 2,2,2-trifluoroethyl, phenyl, 2,6-dimethylphenyl, and a nitrile group.

22. The metal complex of claim 1 , wherein R 1 , R 2 and R 3 are methyl.

23. The metal complex of claim 8 , wherein R t is selected from hydrogen, deuterium or methyl, and R u to R z are each independently selected from hydrogen, deuterium, fluorine, methyl, ethyl, propyl, cyclobutyl, cyclopentyl, cyclohexyl, 3-methylbutyl, 3-ethylpentyl, trifluoromethyl or combinations thereof.