Organic electroluminescent material and device

1. A compound, having a structure of H-L 1 -E;

wherein H has a structure represented by Formula 1:

in Formula 1, A 1 , A 2 and A 3 are, at each occurrence identically or differently, selected from CR; and the ring A, the ring B and the ring C are, at each occurrence identically or differently, selected from an aromatic ring having 6 to 18 carbon atoms or a hetero-aromatic ring having 3 to 18 carbon atoms;

R x represents mono-substitution, multiple substitutions or non-substitution; and

adjacent substituents R, R x can be optionally joined to form a ring;

wherein E has a structure represented by Formula 2-b, Formula 2-d, or Formula 2-f:

wherein Y is, at each occurrence identically or differently, selected from CR y ;

L 1 is selected from a single bond, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or combinations thereof;

wherein R, R x and R y are, at each occurrence identically or differently, 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof.

2. The compound of claim 1 , wherein the H has a structure represented by Formula 1-a:

wherein A 1 to A 3 are, at each occurrence identically or differently, selected from CR; and X 1 to X 10 are, at each occurrence identically or differently, selected from CR x ; wherein R and R x are, at each occurrence identically or differently, 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof; and

wherein adjacent substituents R, R x can be optionally joined to form a ring.

3. The compound of claim 2 , wherein R and R x are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, 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 amino having 0 to 20 carbon atoms, a cyano group, an isocyano group, a sulfanyl group and combinations thereof; and

adjacent substituents R, R x can be optionally joined to form a ring.

4. The compound of claim 2 , wherein at least one of R and R x is selected from deuterium, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms.

5. The compound of claim 2 , wherein for adjacent substituents R in A 1 to A 3 , adjacent substituents R x in X 1 to X 3 , adjacent substituents R x in X 4 to X 6 , and adjacent substituents R x in X 7 to X 10 , at least one of these groups of adjacent substituents is joined to form a ring.

6. The compound of claim 1 , wherein the H is selected from the group consisting of the following structures:

7. The compound of claim 1 ,

wherein R y is, at each occurrence identically or differently, 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 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, a cyano group, and combinations thereof.

8. The compound of claim 1 , wherein in the structure represented by to Formula 2-b, Formula 2-d, or Formula 2-f, Y in the aza 6-membered ring is selected from CR y , and the R y is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms.

9. The compound of claim 6 , wherein the E is selected from the group consisting of the following structures:

10. The compound of claim 1 , wherein L 1 is selected from the group consisting of the following structures:

11. The compound of claim 10 , wherein the compound has a structure of H-L 1 -E, wherein H is selected from the group consisting of H-1 to H-116, L 1 is selected from the group consisting of L-0 to L-25, and E is selected from the group consisting of E-21 to E-40, E-46 to E-73, E-101 to E-127, E-130 to E-151.

12. The compound of claim 1 , wherein the compound is selected from the group consisting of the following structures:

13. An electroluminescent device, comprising:

an anode,

a cathode, and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of H-L 1 -E;

wherein H has a structure represented by Formula 1:

in Formula 1, A 1 , A 2 and A 3 are, at each occurrence identically or differently, selected from CR; and the ring A, the ring B and the ring C are, at each occurrence identically or differently, selected from an aromatic ring having 6 to 18 carbon atoms or a hetero-aromatic ring having 3 to 18 carbon atoms;

R x represents mono-substitution, multiple substitutions or non-substitution; and

adjacent substituents R, R x can be optionally joined to form a ring;

wherein E has a structure represented by Formula 2-b, Formula 2-d, or Formula 2-f:

wherein Y is, at each occurrence identically or differently, selected from CR y ;

L 1 is selected from a single bond, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or combinations thereof;

wherein R, R x and R y are, at each occurrence identically or differently, 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof.

14. The electroluminescent device of claim 13 , wherein the organic layer is a light-emitting layer, and the compound is a host material.

15. The electroluminescent device of claim 14 , wherein the light-emitting layer further comprises a phosphorescent material.

16. The electroluminescent device of claim 15 , wherein the phosphorescent material is a metal complex comprising at least one ligand, wherein the ligand comprises any one of the following structures:

wherein

R a , R b and R c may represent mono-substitution, multiple substitutions or non-substitution, and may each be identical or different at each occurrence;

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

X c and X a are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se and NR N2 ;

R a , R b , R c , R N1 , R N2 , R C1 and R C2 are, at each occurrence identically or differently, 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof; and

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

17. The electroluminescent device of claim 16 , wherein the metal complex comprises at least one ligand, wherein the ligand has the following structure:

wherein R 1 to R 7 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof.

18. The electroluminescent device of claim 16 , wherein the phosphorescent material is an Ir, Pt or Os complex.

19. The electroluminescent device of claim 18 , wherein the phosphorescent material is an Ir complex and has a structure of Ir(L a )(L b )(L c );

wherein L a , L b and L c are, at each occurrence identically or differently, selected from any one of the above ligands.

20. The electroluminescent device of claim 15 , wherein the phosphorescent material is selected from the group consisting of the following structures:

wherein X f is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NR N3 and CR C3 R C4 ;

wherein X c is CR d or N;

R a , R b and R c may represent mono-substitution, multiple substitutions or non-substitution, and may each be identical or different at each occurrence;

R a , R b , R c , Rd, R N3 , R C3 and R C4 are, at each occurrence identically or differently, 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof.

21. A compound formulation, comprising the compound of claim 1 .

22. The compound of claim 4 , wherein at least one of R and R x is selected from deuterium, phenyl, biphenyl or pyridyl.

23. The compound of claim 1 , wherein R y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and combinations thereof.

24. The compound of claim 1 , wherein R y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuryl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl and phenylpyridyl.

25. The compound of claim 8 , wherein the R y is selected from phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuryl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl or phenylpyridyl.

26. The compound of claim 1 , wherein the L 1 is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene and thienylene.