Organic electroluminescent materials and devices

1. A compound having a structure of Formula II

wherein:

each of L 1 , L 2 , L 3 , and L 4 is independently a bidentate N-heterocyclic carbene ligand or a substituted or unsubstituted acetylacetonate ligand with L 1 , L 2 , L 3 , and L 4 each being the same or different,

Z 1 -Z 4 are each independently C or N with at least two being N;

Z 1 -Z 4 each directly coordinate to Ir:

moiety A and moiety B are each independently a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered aromatic rings;

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

each of R A and R B is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, bowl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

any two adjacent R A and R B can be joined or fused to form a ring;

wherein at least one of the following is true:

i) one of moiety A or moiety B is a 5-membered aromatic ring and the other of moiety A or moiety B is a 6-membered aromatic ring;

ii) moiety A comprises three or more fused rings;

iii) moiety B comprises three or more fused rings;

iv) moiety A and moiety B are each a 6-membered aromatic ring and two R A and/or two R B join together to form a 5-membered heterocyclic ring; or

v) L 1 is different than L 2 , and L 3 is different than L 4 .

2. The compound of claim 1 , wherein moiety A and moiety B are both 5-membered aromatic rings or both 6-membered aromatic rings.

3. The compound of claim 1 , wherein each of R A and R B 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.

4. The compound of claim 1 , wherein one of moiety A or moiety B is a 5-membered aromatic ring and the other of moiety A or moiety B is a 6-membered aromatic ring.

5. The compound of claim 1 , wherein L 1 , L 2 , L 3 , and L 4 are each the same.

6. The compound of claim 1 , wherein L 1 is different than L 2 , and L 3 is different than L 4 .

7. The compound of claim 1 , wherein L 1 , L 2 , L 3 , and L 4 are all acetylacetonate ligands or all N-heterocyclic carbene ligands.

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

wherein:

each of R 2 , R 3 , R 5 , and R 6 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;

R 1 , R 4 , R 7 , and R 8 each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

each of R 1 , R 4 , R 7 , R 8 , R 9 , and R 10 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;

when Y is sp 3 hybridized, Y is O, CRR′, NR, SiRR′, or S;

when Y is sp 2 hybridized, Y is CH or N;

when X is sp 3 hybridized, X is S or O;

when X is sp 2 hybridized, X is CH or N; and

any two adjacent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 can be joined or fused to form a ring.

9. 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 compound of claim 1 .

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

Compound 3a and Compound 3b

having the following structure,

wherein, in Compound 3a, R a = methyl,

in Compound 3b, R a = pentan-3-yl,

Compound 5a and Compound 5b

having the following structure

wherein,

in Compound 5a, R a = methyl, and

in Compound 5b, R a = pentan-3-yl,

Compound 6a and Compound 6b

having the following structure

wherein,

in Compound 6a, R a = methyl, and

in Compound 6b, Rª = pentan-3-yl,

Compound 7a and Compound 7b

having the following structure

wherein,

in Compound 7a, Rª = methyl, and

in Compound 7b, R a = pentan-3-yl,

Compound 8a and Compound 8b

having the following structure

wherein,

in Compound 8a, R a = methyl, and

in Compound 8b, R a = pentan-3-yl,

Compound 9a and Compound 9b

having the following structure

wherein,

in Compound 9a, R a = methyl, and

in Compound 9b, R a = pentan-3-yl,

Compound 10a and Compound 10b

having the following structure

wherein,

in Compound 10a, R a = methyl, and

in Compound 10b, R a = pentan-3-yl,

Compound 10a and Compound 10b

having the following structure

wherein,

in Compound 11a, R a = methyl, and

in Compound 11b, R a = pentan-3-yl,

Compound 12a, Compound 12b

Compound 13a, and Compound 13b

having the following structure

wherein,

in Compound 12a, R a = methyl, R 1 = methyl,

in Compound 12b, R a = pentan-3-yl, R 1 = methyl,

in Compound 13a, R a = methyl, R 1 = phenyl, and

in Compound 13b, R a = pentan-3-yl, R 1 = phenyl,

Compound 14a, Compound 14b,

Compound 15a, and Compound 15b

having the following structure

wherein,

in Compound 14a, R a = methyl, R 1 = methyl,

in Compound 14b, R a = pentan-3-yl, R 1 = methyl,

in Compound 15a, R a = methyl, R 1 = phenyl, and

in Compound 15b, Rª = pentan-3-yl, R 1 = phenyl,

Compound 16a, Compound 16b,

Compound 17a, and Compound 17b

having the following structure

wherein,

in Compound 16a, R a = methyl, R 1 = methyl,

in Compound 16b, R a = pentan-3-yl, R 1 = methyl,

in Compound 17a, R a = methyl, R 1 = phenyl, and

in Compound 17b, Rª = pentan-3-yl, R 1 = phenyl,

Compound 18a, Compound 18b

having the following structure

wherein,

in Compound 18a, R a = methyl, and

in Compound 18b, R a = pentan-3-yl.

Compound 19a and Compound 19b

having the following structure

wherein,

in Compound 19a, R a = methyl, and

in Compound 19b, Rª = pentan-3-yl.

Compound 20a and Compound 20b

having the following structure

wherein,

in Compound 20a, Rª = methyl, and

in Compound 20b, R a = pentan-3-yl.

Compound 21a and Compound 21b

having the following structure

wherein,

in Compound 21a, R a = methyl, and

in Compound 21b, R a = pentan-3-yl.

Compound 22a and Compound 22b

having the following structure

wherein,

in Compound 22a, R a = methyl, and

in Compound 22b, R a = pentan-3-yl.

Compound 23a and Compound 23b

having the following structure

wherein,

in Compound 23a, R a = methyl, and

in Compound 23b, R a = pentan-3-yl.

Compound 24a and Compound 24b

having the following structure

wherein,

in Compound 24a, R a = methyl, and

in Compound 24b, R a = pentan-3-yl.

Compound 25a and Compound 25b

having the following structure

wherein,

in Compound 25a, R a = methyl, and

in Compound 25b, R a = pentan-3-yl.

Compound 26a and Compound 26b

having the following structure

wherein,

in Compound 26a, R a = methyl, and

in Compound 26b, R a = pentan-3-yl.

Compound 27a and Compound 27b

having the following structure

wherein,

in Compound 27a, R a = methyl, and

in Compound 27b, R a = pentan-3-yl.

Compound 28a and Compound 28b

having the following structure

wherein,

in Compound 28a, R a = methyl, and

in Compound 28b, R a = pentan-3-yl.

Compound 29a and Compound 29b

having the following structure

wherein,

in Compound 29a, R a = methyl, and

in Compound 29b, R a = pentan-3-yl.

Compound 30a and Compound 30b

having the following structure

wherein,

in Compound 30a, R a = methyl, and

in Compound 30b, R a = pentan-3-yl.

Compound 31a and Compound 31b

having the following structure

wherein,

in Compound 31a, Rª = methyl, and

in Compound 31b, R a = pentan-3-yl.

Compound 32a and Compound 32b

having the following structure

wherein,

in Compound 32a, R a = methyl, and

in Compound 32b, R a = pentan-3-yl.

Compound 33a and Compound 33b

having the following structure

wherein,

in Compound 33a, R a = methyl, and

in Compound 33b, R a = pentan-3-yl.

Compound 36a and Compound 36b

having the following structure

wherein,

in Compound 36a, R a = methyl, and

in Compound 36b, R a = pentan-3-yl.

Compound 39a and Compound 39b

having the following structure

wherein,

in Compound 39a, R 1 = methyl, and

in Compound 39b, R 1 = H.

Compound 40a and Compound 40b

having the following structure

wherein,

in Compound 40a, R1 = methyl, and

in Compound 40b, R1 = H.

Compound 41a and Compound 41b

having the following structure

wherein,

in Compound 41a, R1 = methyl, and

in Compound 41b, R1 = H.

Compound 42a, Compound 42b,

and Compound 42c

having the following structure

wherein,

in Compound 42a, R 1 = 2,4-Me,

in Compound 42b, R 1 = H, and

in Compound 42c, R 1 = 2,4-F.

Compound 47a, Compound 47b, and

Compound 47c having the following structure

wherein,

in Compound 47a, R 1 = 2,4-Me,

in Compound 47b, R 1 = H, and

in Compound 47c, R 1 = 2,4-F.

Compound 53a, Compound 53b,

Compound 53c, and Compound 53d

having the following structure

wherein,

in Compound 53a, R 1 = H, R a = methyl,

in Compound 53b, R 1 = H, Rª = pentan-3-yl,

in Compound 53c, R 1 = Me, R a = methyl, and

in Compound 53d, R 1 = Me, R a = pentan-3-yl.

Compound 54a, Compound 54b,

Compound 54c, and Compound 54d

having the following structure

wherein,

in Compound 54a, R 1 = H, R a = methyl,

in Compound 54b, R 1 = H, R a = pentan-3-yl,

in Compound 54c, R 1 = Me, R a = methyl, and

in Compound 54d, R 1 = Me, R a = pentan-3-yl.

Compound 55a, Compound 55b,

Compound 55c, and Compound 55d

having the following structure

wherein,

in Compound 55a, R 1 = H, Rª = methyl,

in Compound 55b, R 1 = H, R a = pentan-3-yl,

in Compound 55c, R 1 = Me, Rª = methyl, and

in Compound 55d, R 1 = Me, R a = pentan-3-yl.

Compound 56a, R 1 = H, R a = methyl

Compound 56b, R 1 = H, R a = pentan-3-yl

Compound 56c, R 1 = Me, R a = methyl

Compound 56d, R 1 = Me, R a = pentan-3-yl

Compound 57a, R 1 = H, Rª = methyl

Compound 57b, R 1 = H, R a = pentan-3-yl

Compound 57c, R 1 = Me, R a = methyl

Compound 57d, R 1 = Me, R a = pentan-3-yl

Compound 58a, Compound 58b,

Compound 58c, and Compound 58d

having the following structure

wherein,

in Compound 58a, R 1 = H, R a = methyl,

in Compound 58b, R 1 = H, R a = pentan-3-yl,

in Compound 58c, R 1 = Me, R a = methyl, and

in Compound 58d, R 1 = Me, R a = pentan-3-yl.

Compound 59a, Compound 59b,

Compound 59c, and Compound 59d

having the following structure

wherein,

in Compound 59a, R 1 = H, R a = methyl,

in Compound 59b, R 1 = H, R a = pentan-3-yl,

in Compound 59c, R 1 = Me, R a = methyl, and

in Compound 59d, R 1 = Me, R a = pentan-3-yl.

Compound 60c, and Compound 60d

Compound 60a, Compound 60b,

having the following structure

wherein,

in Compound 60a, R 1 = H, Rª = methyl,

in Compound 60b, R 1 = H, Rª = pentan-3-yl,

in Compound 60c, R 1 = Me, R a = methyl, and

in Compound 60d, R 1 = Me, R a = pentan-3-yl.

Compound 61a, Compound 61b, and

Compound 61c having the following structure

wherein,

in Compound 61a, R 1 = neopentyl,

in Compound 61b, R 1 = H, and

in Compound 61c, R 1 = CF 3 ,

and

Compound 64a, Compound 64b, and

Compound 64c having the following structure

wherein,

in Compound 64a, R 1 = neopentyl,

in Compound 64b, R 1 = H, and

in Compound 64c, R 1 = CF 3 .

11. A compound having a structure of

wherein:

each of L 1 , L 2 , L 3 , and L 4 is independently a bidentate N-heterocyclic carbene ligand or a substituted or unsubstituted acetylacetonate ligand with L 1 , L 2 , L 3 , and L 4 each being the same or different,

Z 1 -Z 4 are each independently C or N with at least two being N;

Z 1 -Z 4 each directly coordinate to Ir;

moiety C, moiety D, and moiety E are each independently a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered aromatic rings;

K is selected from the group consisting of B, BR, N, P, CR, SiR, GeR, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;

R C , R D , and R E each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;

each of R, R C , R D and R E 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; and

any two adjacent R, R C , R D and R E can be joined or fused to form a ring,

wherein in Formula III, at least one of the following is true:

i) R C and R D and/or R E are joined or fused to form a ring; or

ii) L 1 is different than L 2 , and L 3 is different than L 4 .

12. The compound of claim 11 , wherein moiety C is directly bonded to moiety D or moiety E, or bonded to moiety D or moiety E by one atom linker selected from the group consisting of C, O, S, Si, and N for Formula III.

13. The compound of claim 11 , wherein moiety C, moiety D, and moiety E are all 6-membered aromatic rings.

14. The compound of claim 11 , wherein moiety C, moiety D, and moiety E are each independently selected from the group consisting of pyrimidine, pyridine, pyridazine, triazine, pyrazine, benzene, imidazole, pyrazole, oxazole, thiazole, and N-heterocycliccarbene.

15. The compound of claim 11 , wherein each of R C , R D , and R E 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.

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

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

Compound 37a and Compound 37b,

Compound 37c, and Compound 37d

having the following structure

wherein,

in Compound 37a, R 1 = H, Rª = methyl,

in Compound 37b, R 1 = H, Rª = pentan-3-yl,

in Compound 37c, R 1 = Me, Rª = methyl, and

in Compound 37d, R 1 = Me, R a = pentan-3-yl.

Compound 38a, Compound 38b,

Compound 38c, and Compound 38d

having the following structure

wherein,

in Compound 38a, R 1 = H, Rª = methyl,

in Compound 38b, R 1 = H, Rª = pentan-3-yl,

in Compound 38c, R 1 = 2,4-F, R a = methyl, and

in Compound 38d, R 1 = 2,4-F, R a = pentan-3-yl.

Compound 49a and Compound 49b

having the following structure

wherein,

in Compound 49a, R 1 = Me, and

in Compound 49b, R 1 = H,

and

Compound 50a, Compound 50b, and

Compound 50c having the following structure

wherein,

in Compound 50a, R 1 = 2,4-Me,

in Compound 50b, R 1 = H, and

in Compound 50c, R 1 = 2,4-F.

18. 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 having a structure of Formula II

wherein:

each of L 1 , L 2 , L 3 , and L 4 is independently a bidentate N-heterocyclic carbene ligand or a substituted or unsubstituted acetylacetonate ligand with L 1 , L 2 , L 3 , and L 4 each being the same or different,

Z 1 -Z 4 are each independently C or N with at least two being N;

Z 1 -Z 4 each directly coordinate to Ir;

moiety A and moiety B are each independently a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered aromatic rings;

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

each of R A and R B is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, bowl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

any two adjacent R A and R B can be joined or fused to form a ring;

wherein at least one of the following is true:

i) one of moiety A or moiety B is a 5-membered aromatic ring and the other of moiety A or moiety B is a 6-membered aromatic ring;

ii) moiety A comprises three or more fused rings:

iii) moiety B comprises three or more fused rings;

iv) moiety A and moiety B are each a 6-membered aromatic ring and two R A and/or two R B join together to form a 5-membered heterocyclic ring: or

v) L 1 is different than L 2 , and L 3 is different than L 4 .

19. The OLED of claim 18 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of naphthalene, fluorene, triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-naphthalene, aza-fluorene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

20. The OLED of claim 19 , wherein the host is selected from the group consisting of:

and combinations thereof.