Organic electroluminescent materials and devices

1. A compound of Formula I

wherein:

ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

X 1 -X 5 are each independently C or N with at least one of X 1 or X 2 being N;

Y 1 and Y 2 are each independently selected from the group consisting of O, S, Se, BR, NR, PR, CRR′, SiRR′, GeRR′;

R A , R B , and R C each independently represents zero, mono, or up to a maximum number of allowed substitutions to its associated ring; and

R, R′, R A , R B , and R C are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and two substituents can be joined or fused to form a ring.

2. The compound of claim 1 , wherein R, R′, R A , R B , and R C are each independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein one of ring A and ring B is a 5-membered heteroaryl ring, the other one of ring A and ring B is a 6-membered aryl or heteroaryl ring.

4. The compound of claim 1 , wherein both ring A and ring B are 5-membered heteroaryl rings.

5. The compound of claim 1 , wherein at least one of ring A and ring B is selected from the group consisting of pyrrole and imidazole.

6. The compound of claim 1 , wherein Y 1 and Y 2 are both NR, Y 1 and Y 2 are both O, or one of Y 1 and Y 2 is NR and the other is O.

7. The compound of claim 1 , wherein at least one of ring A and ring B is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, and thiazole.

8. The compound of claim 1 , wherein X 1 and X 2 are both N.

9. The compound of claim 1 , wherein one of X 1 and X 2 is N and the other is C.

10. The compound of claim 1 , wherein two R A substituents join together to form a ring that is fused to ring A.

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

wherein:

each X 9 -X 16 is independently selected from the group consisting of C and N; and

Y 3 for each occurrence is independently selected from the group consisting of O, S, Se, NR, CRR′, SiRR′, GeRR′, and BR.

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

and wherein ring B is selected from the group consisting of:

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

Compound name

Structure

i, j, k,

Compound I-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound II-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound III-[(i)(j)(k)]

wherein i is an integer from 1 to 90, and j and k are each independently an integer from 1 to 120, and

Compound IV-[(i)(j)(k)]

wherein i and k are each an integer from 1 to 90 and j is an integer from 1 to 120, and

Compound V-[(i)(j)(k)]

wherein i and j are each independently an integer from 1 to 120, and k is an integer from 1 to 90, and

Compound VI-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound VII-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound VIII-[(i)(j)(k)]

wherein i is an integer from 1 to 90, and j and k are each independently an integer from 1 to 120, and

Compound IX-[(i)(j)(k)]

wherein i, j, and k are each an integer from 1 to 120, and

Compound X-[(i)(j)(k)]

wherein i and k are each an integer from 1 to 90 and j is an integer from 1 to 120, and

Compound XI-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound XII-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound XIII-[(i)(j)(k)]

wherein i is an integer from 1 to 120, and j and k are each independently an integer from 1 to 90, and

Compound XIV-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound XV-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound XVI-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound XVII-[(i)(j)(k)]

wherein i, j, and k are each independently an integer from 1 to 120, and

Compound XVIII- [(Ri)(Rj)(Rk)]

wherein i and k are each independently an integer from 1 to 90, and j is an integer from 1 to 120, and

Compound XIX-[(i)(j)(k)]

wherein i is an integer from 1 to 90, and j and k are each independently an integer from 1 to 120, and

Compound XX-[(i)(j)(k)]

wherein i is an integer from 1 to 90, and j and k are each independently an integer from 1 to 120, and

Compound XXI-[(i)(j)(k)]

wherein i and j are each independently an integer from 1 to 120, and k is an integer from 1 to 90, and

Compound XXII-[(i)(j)(k)]

wherein i and j are each independently an integer from 1 to 120, and k is an integer from 1 to 90, and

Compound XXIII-[(i)(j)(k)]

wherein i and k are each an integer from 1 to 90 and j is an integer from 1 to 120, and

Compound XXIV-[(i)(j)(k)]

wherein i and k are each independently an integer from 1 to 90, and j is an integer from 1 to 120, and

wherein R1 to R120 are defined as follows

14. A compound selected from the group consisting of:

15. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound of Formula I

wherein:

ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

X 1 -X 5 are each independently C or N with at least one of X 1 or X 2 being N;

Y 1 and Y 2 are each independently selected from the group consisting of O, S, Se, BR, NR, PR, CRR′, SiRR′, GeRR′;

R A , R B , and R C each independently represents zero, mono, or up to a maximum number of allowed substitutions to its associated ring; and

R, R′, R A , R B , and R C are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and two substituents can be joined or fused to form a ring.

16. The OLED of claim 15 , wherein the organic layer is an emissive layer and the compound is a host.

17. The OLED of claim 15 , wherein the organic layer is an emissive layer and the compound is a fluorescent emitter.

18. The OLED of claim 17 , wherein the first organic layer further comprises a phosphorescent sensitizer, or the OLED further comprises a second organic layer, disposed between the anode and the cathode, and the second organic layer comprises a phosphorescent sensitizer;

wherein the compound is an acceptor; and

wherein the phosphorescent sensitizer is a transition metal complex having at least one ligand, or part of the ligand if the ligand is more than bidentate, selected from the group consisting of:

wherein:

Y 1 to Y 13 are each independently selected from the group consisting of carbon and nitrogen;

Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;

R e and R f can be fused or joined to form a ring;

each R a , R b , R c , and R d independently represents zero, mono, or up to a maximum number of allowed substitutions to its associated ring;

each R a1 , R b1 , R c1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

two adjacent substituents of R a , R b , R c , and R d can be fused or joined to form a ring or form a multidentate ligand.

19. The OLED of claim 16 , wherein the organic layer further comprises a phosphorescent emitter; wherein the phosphorescent emitter is a transition metal complex having at least one ligand, or part of the ligand if the ligand is more than bidentate, selected from the group consisting of:

wherein:

Y 1 to Y 1 are each independently selected from the group consisting of carbon and nitrogen;

Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;

R e and R f can be fused or joined to form a ring;

each R a , R b , R c , and R d independently represents zero, mono, or up to a maximum number of allowed substitutions to its associated ring;

each R a1 , R b1 , R c1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

two adjacent substituents of R a , R b , R c , and R d can be fused or joined to form a ring or form a multidentate ligand.

20. A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound of Formula I

wherein:

ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

X 1 -X 5 are each independently C or N with at least one of X 1 or X 2 being N;

Y 1 and Y 2 are each independently selected from the group consisting of O, S, Se, BR, NR, PR, CRR′, SiRR′, GeRR′;

R A , R B , and R C each independently represents zero, mono, or up to a maximum number of allowed substitutions to its associated ring; and

R, R′, R A , R B , and R C are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and two substituents can be joined or fused to form a ring.