9 membered ring carbazole compounds

1. A compound comprising Formula 1:

wherein

X 1 to X 19 are each independently selected from CR, or N;

R 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 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 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.

2. The compound of claim 1 , wherein X 1 to X 19 are each independent CR.

3. The compound of claim 1 , wherein the compound comprises a Formula 2 structure:

Wherein

R 1 , R 3 , R 4 , and R 5 independently represent mono, di, tri, tetra substitution, or no substitution;

R 2 independently represent mono, di, tri substitution, or no substitution;

R 1 , R 2 , R 3 , R 4 , and R 5 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 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 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.

4. The compound of claim 1 , wherein the compound comprises a structure of any one of Formula 3-6:

Wherein

R 1 , R 3 , R 4 , R 5 , R 6 , and R 7 independently represent mono, di, tri, tetra substitution, or no substitution;

R 2 independently represent mono, di, tri substitution, or no substitution;

X, are each independently selected from the group consisting of O, S, Se, NR′, CR″R′″ and SiR″″R′″″;

Y are each independently selected from the group consisting of O, S, NR′, CR″R′″ and SiR″″R′″″;

R′, R″, R″″, R′″″, R′″″, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 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 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 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;

L is selected from the group consisting of:

Single bond.

5. The compound of claim 1 , wherein the compound comprises a structure of any one of Formula 7-9:

Wherein

R 1 independently represent mono, di, tri, tetra substitution, or no substitution;

R 2 , R 3 , R 4 , and R 5 independently represent mono, multi substitution, or no substitution; said multi substitution refer to a range that includes di substitution, up to the maximum available substitutions of the formula;

Z are each independently selected from the group consisting of O, S, NR′, CR″R′″ and SiR″″R′″″;

R′, R″, R″″, R′″″, R′″″, R 1 , R 2 , R 3 , R 4 , and R 5 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 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 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.

6. The compound of claim 3 , wherein R 1 , and R 2 are each independently selected from the group consisting of:

7. The compound of claim 4 , wherein R 1 , R 2 , R 6 , and R 7 are each independently selected from the group consisting of:

8. The compound of claim 5 , wherein R 1 , and R 2 are each independently selected from the group consisting of:

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

10. An electroluminescent device comprises:

an anode,

a cathode,

and an organic layer, disposed between the anode and the cathode, comprising a compound of Formula 1:

Wherein

X 1 to X 19 are each independently selected from the group consisting of CR, and N;

Wherein R 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 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 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.

11. The device of claim 10 , wherein the organic layer is a charge transporting layer.

12. The device of claim 10 , wherein the organic layer is a charge blocking layer.

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

14. The device of claim 10 , wherein the organic layer further comprises a phosphorescent emitter.

15. The device of claim 14 , wherein the phosphorescent emitter is a metal complex having at least one ligand comprising any of the following structures:

Wherein

R a , R b , and R c can represent mono, multi substitution, or no substitution; said multi substitution refer to a range that includes di substitution, up to the maximum available substitutions of the formula;

X b is independently 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 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 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.

16. The device of claim 10 , wherein the organic layer is an emissive layer and the compound of Formula 1 is a thermally delayed fluorescent dopant.

17. A formulation comprising the compound of claim 1 .