Organic electroluminescent materials and devices

1. A compound having a structure of formula M(L A ) x (L B ) y (L C ) z :

wherein the ligand L A is

wherein the ligand L B is

wherein the ligand L C is

wherein M is a metal having an atomic number greater than 40;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

wherein x+y+z is the oxidation state of the metal M;

wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are each independently selected from C and N;

wherein Z D is selected from N and a carbene carbon;

wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein R 3 represents mono, or di-substitutions, or no substitutions;

wherein R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution;

wherein R 1 and R 2 each independently represent mono, di, or tri-substitution, or no substitutions;

wherein R 4 is selected from the group consisting of 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;

wherein each of R 1 , R 2 , R 3 , R C , R D , R 11 , R 12 , and R 13 are 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;

wherein any adjacent substituents of R 1 , R 2 , R 3 , R 4 , R C , R D , R 11 , R 12 , and R 13 are optionally joined to form a ring; and

wherein at least one of the following:

(i) Z 1 is N,

(ii) Z 2 is N,

(iii) Z 3 is N,

(iv) Z 5 is N,

(v) R 1 is no substitutions, or

(vi) R 1 is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, alkynyl, aryl, furan, thiophene, acyl, carbonyl, carboxylic acids, ester, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

2. The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1 , wherein M is Ir.

4. The compound of claim 1 , wherein the compound has the formula M(L A ) 2 (L C ).

5. The compound of claim 1 , wherein the compound has the foil iula M(L A )(L B ) 2 .

6. The compound of claim 1 , wherein the compound is homoleptic.

7. The compound of claim 1 , wherein the aryl or heteroaryl of R 4 is substituted by one or more substituent selected from the group consisting of deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclobutyl, cyclopentyl, cyclohexyl, and combinations thereof.

8. The compound of claim 1 , wherein R 4 is phenyl substituted at both ortho positions by a substituent selected from the group consisting of deuterium, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclobutyl, cyclopentyl, cyclohexyl, and combinations thereof.

9. The compound of claim 1 , wherein ligand L A has the structure:

wherein R 2′ represents mono, or di-substitutions, or no substitutions;

wherein R 2′ and R 5 are 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 adjacent substituents of R 2′ , and R 5 are optionally joined to form a ring.

10. The compound of claim 9 , wherein R 4 and R 5 are the identical.

11. The compound of claim 1 , wherein L C has the formula:

wherein R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;

wherein at least one of R 6 , R 7 , R 8 , R 9 , or R 10 has at least two C atoms.

12. The compound of claim 1 , wherein ring C is benzene, and ring D is pyridine.

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

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

wherein X 1 , X 2 , X 3 , X 4 , X 1′ , X 2′ , and X 3′ are each independently selected from the group consisting of N and CR″,

wherein each R, R′, and R″ is independently selected from the group consisting of H, alkyl, aryl, heteroaryl, and combinations thereof, and

wherein adjacent R, R′, and R″ substituents are optionally joined to form a fused or unfused ring.

15. The compound of claim 1 , where L C is selected from the group consisting of

16. The compound of claim 13 , wherein the compound is selected from the group consisting of Compound 1 to Compound 312, where compound x has the formula M(L Ak ) 2 (L Cj ), wherein x=24j+k−24, wherein k is an integer from 1 to 24, wherein j is an integer from 1 to 13, and wherein L C is selected from the group consisting of

17. The compound of claim 13 , wherein the compound is selected from the group consisting of Compound 313 to Compound 2112, where compound x has the formula M(L Ak )(L Bj ) 2 , wherein x=(24j+k−24)+312, wherein k is an integer from 1 to 24, wherein j is an integer from 1 to 75, and wherein L B is selected from the group consisting of

wherein X 1 , X 2 , X 3 , X 4 , X 1′ , X 2′ , and X 3′ are each independently selected from the group consisting of N and CR″,

wherein each R, R′, and R″ is independently selected from the group consisting of H, alkyl, aryl, heteroaryl, and combinations thereof, and

wherein adjacent R, R′, and R″ substituents are optionally joined to form a fused or unfused ring.

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

19. A first device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having a formula M(L A ) x (L B ) y (L C ) z :

wherein the ligand L A is

wherein the ligand L B is

wherein the ligand L C is

wherein M is a metal having an atomic number greater than 40;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

wherein x+y+z is the oxidation state of the metal M;

wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are each independently selected from C and N;

wherein Z D is selected from N and a carbene carbon;

wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein R 3 represents mono, or di-substitutions, or no substitutions;

wherein R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution;

wherein R 1 and R 2 each independently represent mono, di, or tri-substitution, or no substitutions;

wherein R 4 is selected from the group consisting of 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;

wherein each of R 1 , R 2 , R 3 , R C , R D , R 11 , R 12 , and R 13 are 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;

wherein any adjacent substituents of R 1 , R 2 , R 3 , R 4 , R C , R D , R 11 , R 12 , and R 13 are optionally joined to form a ring; and

wherein at least one of the following:

(i) Z 1 is N,

(ii) Z 2 is N,

(iii) Z 3 is N,

(iv) Z 5 is N,

(v) R 1 is no substitutions, or

(vi) R 1 is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, alkynyl, aryl, furan, thiophene, acyl, carbonyl, carboxylic acids, ester, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

20. The device of claim 19 , wherein the device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

21. The device of claim 19 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

22. The device of claim 19 , wherein the organic layer further comprises a host, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , and C n H 2n —Ar 1 , or no substitution;

wherein n is from 1 to 10; and

wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

23. The device of claim 19 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

24. The device of claim 19 , wherein the organic layer further comprises a host and the host is selected from the group consisting of

and combinations thereof.

25. The device of claim 19 , wherein the organic layer further comprises a host and the host comprises a metal complex.

26. A formulation comprising a compound having a formula M(L A ) x (L B ) y (L C ) z :

wherein the ligand L A is

wherein the ligand L B is

wherein the ligand L C is

wherein M is a metal having an atomic number greater than 40;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

wherein x+y+z is the oxidation state of the metal M;

wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are each independently selected from C and N;

wherein Z D is selected from N and a carbene carbon;

wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein R 3 represents mono, or di-substitutions, or no substitutions;

wherein R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution;

wherein R 1 and R 2 each independently represent mono, di, or tri-substitution, or no substitutions;

wherein R 4 is selected from the group consisting of 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;

wherein each of R 1 , R 2 , R 3 , R C , R D , R 11 , R 12 , and R 13 are 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;

wherein any adjacent substituents of R 1 , R 2 , R 3 , R 4 , R C , R D , R 11 , R 12 , and R 13 are optionally joined to form a ring; and

wherein at least one of the following:

(i) Z 1 is N,

(ii) Z 2 is N,

(iii) Z 3 is N,

(iv) Z 5 is N,

(v) R 1 is no substitutions, or

(vi) R 1 is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, alkynyl, aryl, furan, thiophene, acyl, carbonyl, carboxylic acids, ester, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.