Indolocarbazole tetraphenylene compounds

1. A compound having formula 1:

Wherein

X 1 to X 16 are each independently selected form the group consisting of C, CR, and N;

L is selected from the group consisting of a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms;

Y is selected form the group consisting of O, S, Se, NR′, and CR″R′″;

R 1 and R 3 represents mono, di, tri, or tetra substitution or no substitution;

R 2 represents mono or di substitution or no substation;

R, R′, R″, R′″, R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Any adjacent substitution can be optionally joined to form a ring or fused structure;

n is 1, 2, 3, or 4;

when n is 2 or more, L, Y, R 1 , R 2 , and R 3 can be the same or different.

2. The compound of claim 1 , wherein none of X 1 to X 16 is N.

3. The compound of claim 1 , wherein at least one of X 1 to X 16 is N.

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

and combinations thereof.

5. The compound of claim 1 , wherein Y is selected from NR′.

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

7. An electroluminescent device comprises:

an anode,

a cathode,

and an organic layer, disposed between the anode and the cathode, comprising a compound having formula 1:

Wherein

X 1 to X 16 are each independently selected form the group consisting of C, CR, and N;

L is selected from the group consisting of a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms;

Y is O, S, Se, NR′, or CR″R′″;

R 1 and R 3 represents mono, di, tri, or tetra substitution or no substitution;

R 2 represents mono or di substitution or no substation;

R, R′, R″, R′″, R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Any adjacent substitution can be optionally joined to form a ring or fused structure;

n is selected from 1, 2, 3, or 4;

when n is 2 or more, L, Y, R 1 , R 2 , and R 3 can be the same or different.

8. The device of claim 7 , wherein the organic layer is a charge transporting layer.

9. The device of claim 7 , wherein the organic layer is a charge blocking layer.

10. The device of claim 7 , wherein the organic layer is an emissive layer and the compound is a host.

11. The device of claim 7 , wherein the organic layer further comprises a phosphorescent emitter.

12. The device of claim 7 , wherein the organic layer further comprises a phosphorescent emitter and the phosphorescent emitter is a metal complex having at least one ligand comprising the structure selected from the group consisting of:

Wherein

R a , R b , and R c can represent mono, di, tri, or tetra substitution or no 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, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Any adjacent substitution can be optionally joined to form a ring.

13. The device of claim 7 , wherein the organic layer is the emissive layer and the compound of formula 1 is the thermally delayed fluorescent dopant.

14. A formulation comprises the compound of claim 1 .