Organic electroluminescent materials and devices

1. A compound having a Pt tetradentate structure, having the formula:

Formula I;

wherein rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

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

wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof;

wherein when n is 1, L 4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof;

when n is 0, L 4 is not present;

wherein R A , R B , R C , R D , R, and R′ 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, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof;

wherein any adjacent R A , R B , R C , R D , R, and R′ are optionally joined to form a ring;

wherein X 1 , X 2 , X 3 , and X 4 each independently selected from the group consisting of carbon and nitrogen;

wherein one of Q 1 , Q 2 , Q 3 , and Q 4 is oxygen, the remaining three of Q 1 , Q 2 , Q 3 , and Q 4 each represents a direct bond so that Pt directly bonds to three of X 1 , X 2 , X 3 , and X 4 ; and

wherein when L 1 , L 2 , L 3 , or L 4 represents a direct bond, the direct bond is not a C—C bond.

2. The compound of claim 1 , wherein two of X 1 , X 2 , X 3 , and X 4 that directly bond to Pt are carbon thus forming Pt—C bonds, and one of X 1 , X 2 , X 3 , and X 4 that directly bond to Pt is nitrogen.

3. The compound of claim 2 , wherein the two Pt—C bonds are in cis configuration.

4. The compound of claim 1 , wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, NR, O, CRR′, SiRR′, and combinations thereof; and

wherein when n is 1, L 4 is selected from the group consisting of a direct bond, NR, O, CRR′, SiRR′, and combinations thereof.

5. The compound of claim 1 , wherein R and R′ are each independently selected from the group consisting of hydrogen, 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, cyclopentyl, cyclohexyl, phenyl, and combinations thereof.

6. The compound of claim 1 , wherein the compound has at least one Pt-carbene bond.

7. The compound of claim 1 , wherein n is 0.

8. The compound of claim 1 , wherein n is 1.

9. The compound of claim 1 , wherein one of the rings A, B, C, and D is phenyl when said ring is bonded to one of the Q 1 , Q 2 , Q 3 and Q 4 that is oxygen.

10. The compound of claim 1 , wherein the rings A, B, C, and D are each independently selected from the group consisting of phenyl, pyridine, and imidazole.

11. The compound of claim 1 , wherein when L 1 , L 2 , L 3 , or L 4 represents a direct bond, the direct bond is a C—N bond.

12. The compound of claim 1 , wherein at least one of L 1 , L 2 , L 3 , and L 4 is not a direct bond.

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

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

15. A device comprising one or more organic light emitting devices, at least one of the 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 Pt tetradentate structure, having the formula:

Formula I;

wherein rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

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

wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof;

wherein when n is 1, L 4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, and combinations thereof;

when n is 0, L 4 is not present;

wherein R A , R B , R C , R D , R, and R′ 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, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof;

wherein any adjacent R A , R B , R C , R D , R, and R′ are optionally joined to form a ring;

wherein X 1 , X 2 , X 3 , and X 4 are each independently selected from the group consisting of carbon and nitrogen;

wherein one of Q 1 , Q 2 , Q 3 , and Q 4 is oxygen, the remaining three of Q 1 , Q 2 , Q 3 , and Q 4 each represent a direct bond so that Pt directly bonds to three of X 1 , X 2 , X 3 , and X 4 ; and

wherein when L 1 , L 2 , L 3 , or L 4 represents a direct bond, the direct bond is not a C—C bond.

16. The device of claim 15 , 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.

17. The device of claim 15 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

18. The device of claim 15 , 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 m H 2m+1 , OC m H 2m+1 , OAr 1 , N(C m H 2m+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C m H 2m+1 , C≡CC m H 2m+1 , Ar 1 , Ar 1 -Ar 2 , and C m H 2m —Ar 1 , or the host has no substitutions;

wherein m 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.

19. The device of claim 15 , 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.

20. The device of claim 15 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.