Organic electroluminescent materials and devices

1. A compound having the formula:

wherein L 1 is O;

wherein R B , R B′ , and R C each represents mono to a maximum possible number of substitutions, or no substitution;

wherein each of R B and R B′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof;

wherein two R D are joined to form a benzo ring fused to the imidazole, and the benzo ring may be further substituted by up to four substituents that are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, partially or fully fluorinated variants thereof, and partially or fully deuterated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof;

wherein R is aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, aryl, heteroaryl, and combinations thereof;

wherein any substitutions in R A , R B , R B′ , R C , and R D may be joined or fused into a ring;

wherein each R A is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, and at least one R A is not hydrogen; and

wherein each R C is independently H or aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

2. The compound of claim 1 , wherein each of R B and R B′ is independently selected from the group consisting of hydrogen, deuterium, alkyl, partially or fully deuterated alkyl, and combinations thereof, and

two R D are joined to form a benzo ring fused to the imidazole, and the benzo ring may be further substituted by up to two substituents that are each independently selected from the group consisting of alkyl, partially or fully fluorinated variants thereof, and partially or fully deuterated variants thereof.

3. The compound of claim 1 , wherein the two adjacent R D substituents that are joined to form a benzo ring are substituted by one or more substituents selected from the group consisting of alkyl, partially and fully deuterated alkyl, and partially and fully fluorinated alkyl.

4. The compound of claim 1 , wherein R is a 6-membered aromatic ring, which can be further substituted.

5. 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 the formula:

wherein L 1 is O;

wherein R B , R B′ , and R C each represents mono to a maximum possible number of substitutions, or no substitution;

wherein each of R B and R B′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof;

wherein two R D are joined to form a benzo ring fused to the imidazole, and the benzo ring may be further substituted by up to four substituents that are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, partially or fully fluorinated variants thereof, and partially or fully deuterated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof;

wherein R is aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, aryl, heteroaryl, and combinations thereof;

wherein any substitutions in R A , R B , R B′ , R C , and R D may be joined or fused into a ring;

wherein each R A is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, and at least one R A is not hydrogen; and

wherein each R C is independently H or aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

6. The OLED of claim 5 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

7. The OLED of claim 5 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of metal complex, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

8. The OLED of claim 5 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

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, comprising a compound having the formula:

wherein L 1 is O;

wherein R B , R B′ , and R C each represents mono to a maximum possible number of substitutions, or no substitution;

wherein each of R B and R B′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof;

wherein two R D are joined to form a benzo ring fused to the imidazole, and the benzo ring may be further substituted by up to four substituents that are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, partially or fully fluorinated variants thereof and partially or fully deuterated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof;

wherein R is aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, aryl, heteroaryl, and combinations thereof;

wherein any substitutions in R A , R B , R B′ , R C , and R D may be joined or fused into a ring;

wherein each R A is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, and at least one R A is not hydrogen; and

wherein each R C is independently H or aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

10. The consumer product of claim 9 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video walls comprising multiple displays tiled together, a theater or stadium screen, and a sign.

11. A formulation comprising the compound of claim 1 .

12. The compound of claim 1 , wherein exactly one R C is aryl, which can be substituted by alkyl or aryl, and can be partially of fully deuterated.

13. The compound of claim 1 , wherein the two adjacent R D substituents that are joined to form a benzo ring are not further substituted.

14. The compound of claim 1 , wherein each R C is H.

15. The compound of claim 12 , wherein the two adjacent R D substituents that are joined to form a benzo ring are substituted by one or more substituents selected from the group consisting of alkyl, partially and fully deuterated alkyl, and partially and fully fluorinated alkyl.

16. The compound of claim 1 , wherein at least one R A is partially or fully fluorinated alkyl or cycloalkyl, partially or fully deuterated alkyl or cycloalkyl, or a combination of both.

17. The compound of claim 1 , wherein the R A para to the Pt is tert-butyl, partially or fully fluorinated tert-butyl, or partially or fully deuterated tert-butyl, and the remaining R A are H.

18. The compound of claim 1 , wherein the compound has the formula Pt(L Ay )(L Bz ), wherein L Ay has the following structures:

L Ay

Structure of L Ay

Ar 1 , R 1

y

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10, and k is an integer from 20 to 25 and 27 to 30, and

y = 30(i − 1) + k

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20 to 25 and 27 to 30, and

y = 30(i − 1) + k + 900

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20 to 25 and 27 to 30, and

y = 30(i − 1) + k + 1800

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20 to 25 and 27 to 30, and

y = 30(i − 1) + k + 2700

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20 to 25 and 27 to 30, and

y = 30(i − 1) + k + 3600

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20 to 25 and 27 to 30, and

y = 30(i − 1) + k + 4500

wherein R 1 = Rk, wherein k is an integer from 20 to 25 and 27 to 30, and

y = k + 7200

wherein R 1 = Rk, wherein k is an integer from 20 to 25 and 27 to 30, and

y = k + 7230

wherein R 1 = Rk, wherein k is an integer from 20 to 25 and 27 to 30, and

y = k + 7260

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = 70(i − 1) + (k − 30) + 7320

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = 70(i − 1) + (k − 30) + 9420

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = 70(i − 1) + (k − 30) + 11520

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = 70(i − 1) + (k − 30) + 13620

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = 70(i − 1) + (k − 30) + 15720

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = 70(i − 1) + (k − 30) + 17820

wherein R 1 = Rk, wherein k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = (k − 30) + 24120

wherein R 1 = Rk, wherein k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = (k − 30) + 24190

wherein R 1 = Rk, wherein k is an integer from 37- 49, 52-61, 63-74, 81-86, and 95-96, and

y = (k − 30) + 24260

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = 100(i − 1) + k + 24400

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = 100(i − 1) + k + 27400

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = 100(i − 1) + k + 27400

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = 100(i − 1) + k + 30400

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = 100(i − 1) + k + 36400

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = 100(i − 1) + k + 39400

wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 10 and k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = 100(i − 1) + k + 42400

wherein R 1 = Rk, wherein k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = k + 48400

wherein R 1 = Rk, wherein k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = k + 48500

wherein R 1 = Rk, wherein k is an integer from 20- 25, 27-30, 37-49, 52-61, 63-74, 81-86, and 95-96, and

y = k + 48600

wherein L Bz has the following structures:

L Bz

L Bz structure

Ar 2 , Ar 3 , R 2

Z

wherein Ar 2 = Aj, wherein j is an integer from 11-18 and 21-30, and

z = j

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 31

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 961

wherein Ar 2 = Aj, wherein j is an integer from 11-18 and 21-30, and

z = j + 1891

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 1921

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 2821

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 3721

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 4651

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 5581

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 6481

z = 7382

wherein Ar 2 = Aj, wherein j is an integer from 11 to 18 and 21 to 30, and

z = j + 7382

wherein Ar 2 = Aj, wherein j is an integer from 11 to 18 and 21 to 30, and

z = j + 7412

wherein Ar 2 = Aj, wherein j is an integer from 11 to 18 and 21 to 30, and

z = j + 7442

wherein Ar 2 = Aj, wherein j is an integer from 11 to 18 and 21 to 30, and

z = j + 7472

wherein Ar 2 = Aj, wherein j is an integer from 11-18 and 21-30, and

z = j + 19686

z = 19717

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 19717

wherein Ar 2 = Aj, wherein j is an integer from 11 to 18 and 21 to 30, and

z = j + 20617

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 20647

wherein Ar 2 = Aj, wherein j is an integer from 11 to 18 and 21 to 30, and

z = j + 21547

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 23437

wherein Ar 2 = Aj, wherein j is an integer from 11 to 18 and 21 to 30, and

z = j + 24337

wherein Ar 2 = Aj and Ar 3 = Am, wherein each of j and m is independently an integer from 11-18 and 21-30, and

z = 30(j − 1) + m + 24367

wherein Ar 2 = Aj, wherein j is an integer from 11 to 18 and 21 to 30, and

z = j + 25267

wherein A1 to A18 and A21 to A30 have the following structures:

and

wherein R20-R25, R27-R30, R37-R49, R52-R61, R63-R74, R81-R86, and R95-R96 have the following structures: