Organic electroluminescent materials and devices

1. A compound of Formula I:

wherein:

X 1 -X 8 are each independently C or N, wherein two adjacent X 1 -X 8 are carbon-fused to a structure of Formula II:

X 9 -X 12 are each independently C or N;

A 1 , A 2 , and A 3 are each independently selected from the group consisting of O, S, Se, N, NR, CR, CRR′, SiR, SiRR′, GeR, and GeRR′, with at least one of A 1 and A 2 being N or NR;

each occurrence of is independently a single bond or a double bond, wherein one occurrence of is a single bond and one occurrence of is a double bond;

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

each of occurrence R, R′, R A , R B , and R c is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, 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, with at least one of R, R′, R A , R B , and R c comprising a group of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, or Formula IX:

each occurrence of Y 1 , Y 2 , and Y 3 is independently absent, O, S, Se, NR, CRR′, SiRR′, or GeRR′;

each occurrence of Ar′ and Ar 2 is independently an optionally substituted aryl group or an optionally substituted heteroaryl group, wherein Ar′ and Ar 2 are optionally joined or fused together to form a ring;

each occurrence of X 13 -X 20 is independently C or N, with the proviso that at least one of X 13 -X 20 is N;

each occurrence of A 4 is selected from the group consisting of O, S, Se, NR, CRR′, SiRR′, and GeRR′;

each occurrence of R X independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;

each occurrence of R X is 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,

each occurrence of R Y is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula IX, 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;

the maximum number of N atoms that are connected to each other within a ring is two; and

any two substituents are optionally joined or fused together to form a ring.

2. The compound of claim 1 , wherein each of R, R′, R A , R B , R c , R X , and R Y is 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 A 1 and A 2 is N and the other is NR.

4. The compound of claim 1 , wherein A 3 is NR.

5. The compound of claim 1 , wherein X 1 -X 8 are each independently C.

6. The compound claim 1 , wherein X 9 -X 12 are each independently C.

7. The compound of claim 1 , wherein one of X 1 -X 8 is N.

8. The compound of claim 1 , wherein one of X 9 -X 12 is N.

9. The compound of claim 1 , wherein Y 1 and Y 2 are each independently O, and Y 3 is absent.

10. The compound of claim 1 , wherein Y 1 , Y 2 , and Y 3 are each independently O.

11. The compound of claim 1 , wherein A 4 is NR.

12. The compound of claim 1 , wherein the compound has the following Formula:

wherein X 1 -X 12 , A 1 -A 3 , R A , R B , and R C are each as defined in claim 1 .

13. The compound of claim 1 , wherein the compound has the following Formula:

wherein X 1 -X 12 , R, R A , and R B each as defined in claim 1 .

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

wherein X 1 -X 20 R, R X , R Y , R A -R C , A 3 -A 4 , Y 1 -Y 3 , and Ar 1 -Ar 2 are each as defined in claim 1 .

15. The compound of claim 1 , wherein the compound of Formula I is selected from the group consisting of:

wherein the compound comprises a substituent comprising a group of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, or Formula IX, and

wherein each ring of each of the above core structures is further independently optionally substituted from zero up to a maximum allowed substitution with its associated ring by 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, wherein any two substituents are optionally joined or fused together to form a ring.

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

17. 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:

X 1 -X 8 are each independently C or N, wherein two adjacent X 1 -X 8 are carbon-fused to a structure of Formula II:

X 9 -X 12 are each independently C or N;

A 1 , A 2 , and A 3 are each independently selected from the group consisting of O, S, Se, N, NR, CR, CRR′, SiR, SiRR′, GeR, and GeRR′, with at least one of A 1 and A 2 being N or NR;

each occurrence of is independently a single bond or a double bond, wherein one occurrence of is a single bond and one occurrence of is a double bond;

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

each of occurrence R, R′, R A , R B , and R c is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, 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, with at least one of R, R′, R A , R B , and R c comprising a group of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, or Formula IX:

each occurrence of Y 1 , Y 2 , and Y 3 is independently absent, 0, S, Se, NR, CRR′, SiRR′, or GeRR′;

each occurrence of Ar 1 , and Ar 2 is independently an optionally substituted aryl group or an optionally substituted heteroaryl group, wherein Ar 1 and Ar 2 are optionally joined or fused together to form a ring;

each occurrence of X 13 -X 20 is independently C or N, with the proviso that at least one of X 13 -X 20 is N;

each occurrence of A 4 is selected from the group consisting of O, S, Se, NR, CRR′, SiRR′, and GeRR′;

each occurrence of R X independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;

each occurrence of R X is 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;

each occurrence of R Y is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula IX, 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;

the maximum number of N atoms that are connected to each other within a ring is two; and

any two substituents are optionally joined or fused together to form a ring.

18. The OLED of claim 17 , wherein the compound is a host, and the organic layer is an emissive layer that comprises a phosphorescent emitter and 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 each Y 1 to Y 13 are independently selected from the group consisting of carbon and nitrogen;

wherein Y′ is selected from the group consisting of B R e , N R e , P R e , 0, S, Se, C═O, S═O, SO 2 , CR e R f , Si R e R f , and GeR e R f ;

wherein R e and R f are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

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

wherein two adjacent substituents of R a , R b , R e , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

19. 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:

X 1 -X 8 are each independently C or N, wherein two adjacent X 1 -X 8 are carbon-fused to a structure of Formula II:

X 9 -X 12 are each independently C or N;

A 1 , A 2 , and A 3 are each independently selected from the group consisting of O, S, Se, N, NR, CR, CRR′, SiR, SiRR′, GeR, and GeRR′, with at least one of A 1 and A 2 being N or NR;

each occurrence of is independently a single bond or a double bond, wherein one occurrence of is a single bond and one occurrence of is a double bond;

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

each of occurrence R, R′, R A , R B , and R c is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, 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, with at least one of R, R′, R A , R B , and R c comprising a group of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, or Formula IX:

each occurrence of V, Y 2 , and Y 3 is independently absent, 0, S, Se, NR, CRR′, SiRR′, or GeRR′;

each occurrence of Ar 1 , and Ar 2 is independently an optionally substituted aryl group or an optionally substituted heteroaryl group, wherein Ar 1 and Ar 2 are optionally joined or fused together to form a ring;

each occurrence of X 13 -X 20 is independently C or N, with the proviso that at least one of X 13 -X 20 is N;

each occurrence of A 4 is selected from the group consisting of O, S, Se, NR, CRR′, SiRR′, and GeRR′;

each occurrence of R X independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;

each occurrence of R X is 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;

each occurrence of R Y is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula IX, 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;

the maximum number of N atoms that are connected to each other within a ring is two; and

any two substituents are optionally joined or fused together to form a ring.

20. A formulation comprising a compound according claim 1 .