Organic electroluminescent materials and devices

1. A compound of Formula I

wherein M is Pt or Pd;

wherein ring A is a 5-membered or 6-membered aromatic ring;

wherein X 1 to X 6 are each independently C or N, provided that X 1 to X 3 are not all N;

wherein n is 0 or 1; when n is 1, L is present and selected from the group consisting of O, S, Se, NR, BR, CRR′, SiRR′, C═O, S═O, SO 2 , NR—CRR′, CRR′—CRR′, SiRR′—SiRR′, SiRR′—CRR′; when n is 0, L is not present;

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

wherein each R 1 , R, R′, R A , R B , 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein R 2 is

wherein each R 1′ and R 2′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one of R 1′ and R 2′ is not hydrogen or deuterium; and

wherein B is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted;

wherein R 1 can be joined with R E ; and

wherein any two substituents can be joined or fused together to form a ring.

2. The compound of claim 1 , wherein each R 1 , R 2 , R, R′, R A , R B , 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, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein X 1 to X 5 are each C.

4. The compound of claim 1 , wherein at least one of X 1 to X 5 is N.

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

6. The compound of claim 1 , wherein at least one of the following two conditions is true:

(1) two R D are joined together to form a fused aromatic ring or rings, which can be further substituted; and

(2) two R E are joined together to form a fused aromatic ring or rings, which can be further substituted.

7. The compound of claim 1 , wherein at least one R C is selected from the group consisting of aryl, alkyl, and combination thereof.

8. The compound of claim 1 , wherein R 1 and R E are joined to form a linker comprising one backbone atom, a linker comprising two backbone atoms, or a linker comprising three or more backbone atoms.

9. The compound of claim 1 , wherein X 6 is N.

10. The compound of claim 1 , wherein X 6 is C.

11. The compound of claim 1 , wherein n is 1, and L is selected from the group consisting of O, S, NR, CRR′, and SiRR′.

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

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

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

wherein m is 0 or 1; when m is 1, L′ is present and selected from the group consisting of O, S, Se, NR, BR, CRR′, SiRR′, C═O, S═O, SO 2 , NR—CRR′, CRR′—CRR′, SiRR′—SiRR′, SiRR′—CRR′; when m is 0, L′ is not present; and

wherein any two substituents may be joined or fused together to form a ring.

13. The compound of claim 1 , wherein the compound is one of Compound x having the formula Pt(L Ay )(L Bz ),

wherein x is an integer defined by x=41160(z−1)+y,

wherein y is an integer from 1 to 41160 and z is an integer from 1 to 560,

wherein L Ay have the following structures:

Structure of L Ay

y

Ar 1 , R 1

for L A1 to L A2100

wherein y = 70(i − 1) + k, wherein i is an integer 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai from and R 1 = Rk,

for L A2101 -L A4200

wherein y = 70(i − 1) + k + 2100, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A4201 -L A6300

wherein y = 70(i − 1) + k + 4200, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A6301 -L A8400

wherein y = 70(i − 1) + k + 6300, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A8401 -L A10500

wherein y = 70(i − 1) + k + 8400, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A10501 -L A12600

wherein y = 70(i − 1) + k + 10500, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A12601 -L A14700

wherein y = 70(i − 1) + k + 12600, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A14701 -L A16800

wherein y = 70(i − 1) + k + 14700, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A16801 to L A16870

wherein y = k + 16800, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A16871 -L A16940

wherein y = k + 16870, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A16941 -L A17010

wherein y = k + 16940, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A17011 -L A17080

wherein y = k + 17010, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A17081 to L A19180

wherein y = 70(i − 1) + k + 17080, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A19181 to L A21280

wherein y = 70(i − 1) + k + 19180, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A21281 to L A23380

wherein y = 100(i − 1) + k + 21280, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A23381 to L A25480

wherein y = 100(i − 1) + k + 23380, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A25481 to L A27580

wherein y = 100(i − 1) + k + 25480, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A27581 to L A29680

wherein y = 100(i − 1) + k + 27580, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A29681 to L A31780

wherein y = 100(i − 1) + k + 29680, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A31781 to L A33880

wherein y = 100(i − 1) + k + 31780, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A33881 to L A35980

wherein y = 100(i − 1) + k + 33880, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A35981 to L A36050

wherein y = k + 35980, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36051 to L A36120

wherein y = k + 36050, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36121 to L A36190

wherein y = k + 36120, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36191 to L A36260

wherein y = k + 36190, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36261 to L A36330

wherein y = k + 36260, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36331 to L A36470

wherein y = k + 36330, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36471 to L A36540

wherein y = k + 36470, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36541 to L A36610

wherein y = k + 36540, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36611 to L A36680

wherein y = k + 36610, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36681 to L A36750

wherein y = k + 36680, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36751 to L A36820

wherein y = k + 36750, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36821 to L A36890

wherein y = k + 36820, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36891 - L A36960

wherein y = k + 36890, wherein k is an integer from 1 to 70, and

wherein R 1 = Rk,

for L A36961 -L A39060

wherein y = 30(i − 1) + k + 36960, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

for L A39061 -L A41160

wherein y = 30(i − 1) + k + 39060, wherein i is an integer from 1 to 30 and k is an integer from 1 to 70, and

wherein Ar 1 = Ai and R 1 = Rk,

wherein L Bz has the following structures:

Structure of L Bz

z

R 2

for L B1 -L B70

wherein z = j, wherein j is an integer from 1 to 70, and

wherein R 2 = Rj,

for L B71 -L B140

wherein z = j + 70, wherein j is an integer from 1 to 70, and

wherein R 2 = Rj,

for L B141 -L B210

wherein z = j + 140, wherein j is an integer from 1 to 70, and

wherein R 2 = Rj,

for L B211 -L B280

wherein z = j + 210, wherein j is an integer from 1 to 70, and

wherein R 2 = Rj,

for L B281 -L B350

wherein z = j + 280, wherein j is an integer from 1 to 70, and

wherein R 2 = Rj,

for L B351 -L B420

wherein z = j + 350, wherein j is an integer from 1 to 70, and

wherein R 2 = Rj,

for L B421 -L B490

wherein z = j + 420, wherein j is an integer from 1 to 70, and

wherein R 2 = Rj,

for L B491 -L B560

wherein z = j + 490, wherein j is an integer from 1 to 70, and

wherein R 2 = Rj,

wherein A1 to A30 have the following structures:

and wherein R1 to R70 have the following structures:

14. 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 of Formula I

wherein M is Pt or Pd;

wherein ring A is a 5-membered or 6-membered aromatic ring;

wherein X 1 to X 6 are each independently C or N, provided that X 1 to X 3 are not all N;

wherein n is 0 or 1; when n is 1, L is present and selected from the group consisting of O, S, Se, NR, BR, CRR′, SiRR′, C═O, S═O, SO 2 , NR—CRR′, CRR′—CRR′, SiRR′—SiRR′, SiRR′—CRR′; when n is 0, L is not present;

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

wherein each R 1 , R, R′, R A , R B , 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein R 2 is

wherein each R 1′ and R 2′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one of R 1′ and R 2′ is not hydrogen or deuterium; and

wherein B is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted;

wherein R 1 can be joined with R E ; and

wherein any two substituents can be joined or fused together to form a ring.

15. The OLED of claim 14 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

16. The OLED of claim 14 , wherein the compound is a sensitizer and the OLED further comprises an acceptor; and wherein the acceptor is selected from the group consisting of fluorescent emitter, delayed fluorescence emitter, and combination thereof.

17. 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 of Formula I

wherein M is Pt or P;

wherein ring A is a 5-membered or 6-membered aromatic ring;

wherein X 1 to X 6 are each independently C or N, provided that X 1 to X 3 are not all N;

wherein n is 0 or 1; when n is 1, L is present and selected from the group consisting of O, S, Se, NR, BR, CRR′, SiRR′, C═O, S═O, SO 2 , NR—CRR′, CRR′—CRR′, SiRR′—SiRR′, SiRR′—CRR′; when n is 0, L is not present;

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

wherein each R 1 , R, R′, R A , R B , 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein R 2 is

wherein each R 1′ and R 2′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one of R 1′ and R 2′ is not hydrogen or deuterium; and

wherein B is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted;

wherein R 1 can be joined with R E ; and

wherein any two substituents can be joined or fused together to form a ring.

18. The compound of claim 1 , wherein at least one of R 1 , R 2 , R, R′, R A , R B , R C , R D , and R E comprises a chemical group containing at least three 6-membered aromatic rings that are not fused next to each other.

19. The compound of claim 13 , wherein the compound is selected from the group consisting of those compounds among Compound x having the formula Pt(L Ay )(L Bz ), in which the variable Ai in the definition for the ligand L Ay is one of A1, A2, A3, A7, A10, A11, A12, A13, A19, A20, A21, A23, and A29, or

the compound is selected from the group consisting of those compounds among Compound x having the formula Pt(L Ay )(L Bz ), in which the variable R 1 in the definition for the ligand L Ay is one of R1, R2, R3, R4, R8, R12, R13, R14, R15, R16, R17, R18, R19, R20, R27, R28, R29, R34, R41, R42, R48, R49, R68, R69, and R70.