Organic electroluminescent materials and devices

1. A compound having Formula I:

Formula I;

wherein G is selected from the group consisting of:

wherein G 1 is a six-member aryl or heteroaryl ring;

wherein L 1 is a direct bond or an organic linker;

wherein n 1 and n 2 are independently an integer of 0 or 1; when n 1 or n 2 is 0, L 2 or L 3 is not present; and when n 1 or n 2 is 1, L 2 or L 3 is independently selected from the group consisting of a direct bond, oxygen, CR 1 R 2 , NR 3 , and SiR 4 R 5 ;

wherein Z 1 , Z 2 , and Z 4 to Z 32 are each independently selected from the group consisting of N and CR 6 ;

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of aryl and heteroaryl;

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents can optionally join or fuse into a ring;

where each R 6 is independently selected from the group consisting of a direct bond, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent substituents can optionally join or fuse into a ring; and

wherein G 1 , Ar 1 , and Ar 2 each can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents can optionally join or fuse into a ring;

provided that R 6 does not comprise a carbazole;

provided that when Z 9 to Z 16 are each CR 6 , then no adjacent groups R 6 at Z 9 to Z 16 join or fuse into a ring;

and further provided that when G 1 is a 6-membered aryl ring, Z 1 , Z 2 , and Z 4 -Z 32 are CR 6 , R 6 is hydrogen, and n 1 is 0, then Ar 1 is not unsubstituted phenyl;

and wherein when G is

at least one of the following is true:

i) Ar 2 is not a dibenzofuran or dibenzothiophene;

ii) Ar 2 is a dibenzofuran or dibenzothiophene, and at least one of Z 1 -Z 2 , Z 4 -Z 8 , and Z 17 -Z 32 is N; or

iii) n 2 is not 0.

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

wherein Z 33 to Z 38 are each independently selected from the group consisting of N and CR 6 .

3. The compound of claim 1 , wherein Z 1 , Z 2 , and Z 4 to Z 32 are each independently a CR 6 .

4. The compound of claim 2 , wherein Z 1 , Z 2 , and Z 4 to Z 32 are each independently a CR 6 .

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

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

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having Formula I:

Formula I;

wherein G is selected from the group consisting of:

wherein G 1 is a six-member aryl or heteroaryl ring;

wherein L 1 is a direct bond or an organic linker;

wherein n 1 and n 2 are independently an integer of 0 or 1; when n 1 or n 2 is 0, L 2 or L 3 is not present; and when n 1 or n 2 is 1, L 2 or L 3 is independently selected from the group consisting of a direct bond, oxygen, CR 1 R 2 , NR 3 , and SiR 4 R 5 ;

wherein Z 1 , Z 2 , and Z 4 to Z 32 are each independently selected from the group consisting of N and CR 6 ;

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of aryl and heteroaryl;

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents can optionally join or fuse into a ring;

where each R 6 is independently selected from the group consisting of a direct bond, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent substituents can optionally join or fuse into a ring; and

wherein G 1 , Ar 1 , and Ar 2 each can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents can optionally join or fuse into a ring;

provided that R 6 does not comprise a carbazole;

provided that when Z 9 to Z 16 are each CR 6 , then no adjacent groups R 6 at Z 9 to Z 16 join or fuse into a ring;

and further provided that when G 1 is a 6-membered aryl ring, Z 1 , Z 2 , and Z 4 -Z 32 are CR 6 , R 6 is hydrogen, and n 1 is 0, then Ar 1 is not unsubstituted phenyl;

and wherein when G is

at least one of the following is true:

i) Ar 2 is not a dibenzofuran or dibenzothiophene;

ii) Ar 2 is a dibenzofuran or dibenzothiophene, and at least one of Z 1 -Z 2 , Z 4 -Z 8 , and Z 17 -Z 32 is N; or

iii) n 2 is not 0.

7. The OLED of claim 6 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.

8. The OLED of claim 6 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant 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 X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;

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

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;

wherein R′, R″, R a , R b , R c , and R d are each 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 acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

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

9. The OLED of claim 6 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer.

10. The OLED of claim 6 , wherein the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer.

11. The OLED of claim 6 , wherein the OLED is incorporated into a device is selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.

12. A formulation comprising a compound having Formula I:

Formula I;

wherein G is selected from the group, consisting of:

wherein G 1 is a six-member aryl or heteroaryl ring;

wherein L 1 is a direct bond or an organic linker;

wherein n 1 and n 2 are independently an integer of 0 or 1; when n 1 or n 2 is 0, L 2 or L 3 is not present; and when n 1 or n 2 is 1, L 2 or L 3 is independently selected from the group consisting of a direct bond, oxygen, CR 1 R 2 , NR 3 , and SiR 4 R 5 ;

wherein Z 1 , Z 2 , and Z 4 to Z 32 are each independently selected from the group consisting of N and CR 6 ;

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of aryl and heteroaryl;

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents can optionally join or fuse into a ring;

where each R 6 is independently selected from the group consisting of a direct bond, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent substituents can optionally join or fuse into a ring; and

wherein G 1 , Ar 1 , and Ar 2 each can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents can optionally join or fuse into a ring;

provided that R 6 does not comprise a carbazole;

provided that when Z 9 to Z 16 are each CR 6 , then no adjacent groups R 6 at Z 9 to Z 16 join or fuse into a ring;

and further provided that when G 1 is a 6-membered aryl ring, Z 1 , Z 2 , and Z 4 -Z 32 are CR 6 , R 6 is hydrogen, and n 1 is 0, then Ar 1 is not unsubstituted phenyl;

and wherein when G is

at least one of the following is true:

i) Ar 2 is not a dibenzofuran or dibenzothiophene;

ii) Ar 2 is a dibenzofuran or dibenzothiophene, and at least one of Z 1 -Z 2 , Z 4 -Z 8 , and Z 17 -Z 32 is N; or

iii) n 2 is not 0.