Organic electroluminescent materials and devices
This invention discloses novel ligands for metal complexes. These ligands contain a phenyl with an iso-quinoline (or other type of heterocycles) which are bridged together with a carbon substituted by two aliphatic side chains. The resulting light-emitting metal complexes exhibited high external quantum efficiency and better line shape.
1. A compound 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 X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are each independently a CR or N;
wherein X 7 is CH;
wherein X 8 is carbon or nitrogen;
wherein when X 6 is a CR, R is hydrogen;
wherein Y is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R CC , and R DD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein each of R, R′, R″, R CC , and R DD 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 each of R X , R Y , and R Z are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein each of R X , R Y , and R Z do not comprise alkenyl,
wherein when X 1 to X 5 is carbon, then R 1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof; and when R 1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
wherein when at least one of X 1 to X 5 is nitrogen, then R 1 is 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 1 , R, R′, R CC , R DD , R X , R Y , and R Z are optionally joined or fused into a ring.
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 selected from the group consisting of M(L A ) 2 (L C ) and M(L A )(L B ) 2 .
5. The compound of claim 1 , wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , and X 7 are each a carbon.
6. The compound of claim 1 , wherein one of X 1 , X 2 , X 3 , X 4 , and X 5 is nitrogen, and the rest of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , and X 7 are carbon.
7. The compound of claim 1 , wherein Y is CR′R″.
8. The compound of claim 1 , wherein ring C is benzene, and ring D is pyridine of which X 8 is N.
9. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
wherein each R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , and R 20 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.
10. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
L A1 to L A165 based on the following formula:
R A
R B
R C
R D
R E
Y
L A1
H
H
H
H
H
C(CH 3 ) 2
L A2
H
R B1
H
H
H
C(CH 3 ) 2
L A3
H
R B2
H
H
H
C(CH 3 ) 2
L A4
H
R B3
H
H
H
C(CH 3 ) 2
L A5
H
R B4
H
H
H
C(CH 3 ) 2
L A6
H
R B5
H
H
H
C(CH 3 ) 2
L A7
H
R A2
H
H
H
C(CH 3 ) 2
L A8
H
R A22
H
H
H
C(CH 3 ) 2
L A9
H
R A28
H
H
H
C(CH 3 ) 2
L A10
H
H
H
H
H
NCH 3
L A11
H
R B1
H
H
H
NCH 3
L A12
H
R B2
H
H
H
NCH 3
L A13
H
R B3
H
H
H
NCH 3
L A14
H
R B4
H
H
H
NCH 3
L A15
H
R B5
H
H
H
NCH 3
L A16
H
R A2
H
H
H
NCH 3
L A17
H
R A22
H
H
H
NCH 3
L A18
H
R A28
H
H
H
NCH 3
L A19
H
H
H
H
H
S
L A20
H
R B1
H
H
H
S
L A21
H
R B2
H
H
H
S
L A22
H
R B3
H
H
H
S
L A23
H
R B4
H
H
H
S
L A24
H
R B5
H
H
H
S
L A25
H
R A2
H
H
H
S
L A26
H
R A22
H
H
H
S
L A27
H
R A28
H
H
H
S
L A28
H
H
H
H
H
O
L A29
H
R B1
H
H
H
O
L A30
H
R B2
H
H
H
O
L A31
H
R B3
H
H
H
O
L A32
H
R B4
H
H
H
O
L A33
H
R B5
H
H
H
O
L A34
H
R A2
H
H
H
O
L A35
H
R A22
H
H
H
O
L A36
H
R A28
H
H
H
O
L A37
H
H
H
H
H
Si(CH 3 ) 2
L A38
H
R B1
H
H
H
Si(CH 3 ) 2
L A39
H
R B2
H
H
H
Si(CH 3 ) 2
L A40
H
R B3
H
H
H
Si(CH 3 ) 2
L A41
H
R B4
H
H
H
Si(CH 3 ) 2
L A42
H
R B5
H
H
H
Si(CH 3 ) 2
L A43
H
R A2
H
H
H
Si(CH 3 ) 2
L A44
H
R A22
H
H
H
Si(CH 3 ) 2
L A45
H
R A28
H
H
H
Si(CH 3 ) 2
L A46
H
H
R B1
H
H
C(CH 3 ) 2
L A47
H
H
R B2
H
H
C(CH 3 ) 2
L A48
H
H
R B3
H
H
C(CH 3 ) 2
L A49
H
H
R B4
H
H
C(CH 3 ) 2
L A50
H
H
R B5
H
H
C(CH 3 ) 2
L A51
H
H
R A2
H
H
C(CH 3 ) 2
L A52
H
H
R A22
H
H
C(CH 3 ) 2
L A53
H
H
R A28
H
H
C(CH 3 ) 2
L A54
H
H
R B1
H
H
NCH 3
L A55
H
H
R B2
H
H
NCH 3
L A56
H
H
R B3
H
H
NCH 3
L A57
H
H
R B4
H
H
NCH 3
L A58
H
H
R B5
H
H
NCH 3
L A59
H
H
R A2
H
H
NCH 3
L A60
H
H
R A22
H
H
NCH 3
L A61
H
H
R A28
H
H
NCH 3
L A62
H
H
R B1
H
H
S
L A63
H
H
R B2
H
H
S
L A64
H
H
R B3
H
H
S
L A65
H
H
R B4
H
H
S
L A66
H
H
R B5
H
H
S
L A67
H
H
R A2
H
H
S
L A68
H
H
R A22
H
H
S
L A69
H
H
R A28
H
H
S
L A70
H
H
R B1
H
H
O
L A71
H
H
R B2
H
H
O
L A72
H
H
R B3
H
H
O
L A73
H
H
R B4
H
H
O
L A74
H
H
R B5
H
H
O
L A75
H
H
R A2
H
H
O
L A76
H
H
R A22
H
H
O
L A77
H
H
R A28
H
H
O
L A78
H
H
R B1
H
H
Si(CH 3 ) 2
L A79
H
H
R B2
H
H
Si(CH 3 ) 2
L A80
H
H
R B3
H
H
Si(CH 3 ) 2
L A81
H
H
R B4
H
H
Si(CH 3 ) 2
L A82
H
H
R B5
H
H
Si(CH 3 ) 2
L A83
H
H
R A2
H
H
Si(CH 3 ) 2
L A84
H
H
R A22
H
H
Si(CH 3 ) 2
L A85
H
H
R A28
H
H
Si(CH 3 ) 2
L A86
H
H
H
R B1
H
C(CH 3 ) 2
L A87
H
H
H
R B2
H
C(CH 3 ) 2
L A88
H
H
H
R B3
H
C(CH 3 ) 2
L A89
H
H
H
R B4
H
C(CH 3 ) 2
L A90
H
H
H
R B5
H
C(CH 3 ) 2
L A91
H
H
H
R A2
H
C(CH 3 ) 2
L A92
H
H
H
R A22
H
C(CH 3 ) 2
L A93
H
H
H
R A28
H
C(CH 3 ) 2
L A94
H
H
H
R B1
H
NCH 3
L A95
H
H
H
R B2
H
NCH 3
L A96
H
H
H
R B3
H
NCH 3
L A97
H
H
H
R B4
H
NCH 3
L A98
H
H
H
R B5
H
NCH 3
L A99
H
H
H
R A2
H
NCH 3
L A100
H
H
H
R A22
H
NCH 3
L A101
H
H
H
R A28
H
NCH 3
L A102
H
H
H
R B1
H
S
L A103
H
H
H
R B2
H
S
L A104
H
H
H
R B3
H
S
L A105
H
H
H
R B4
H
S
L A106
H
H
H
R B5
H
S
L A107
H
H
H
R A2
H
S
L A108
H
H
H
R A22
H
S
L A109
H
H
H
R A28
H
S
L A110
H
H
H
R B1
H
O
L A111
H
H
H
R B2
H
O
L A112
H
H
H
R B3
H
O
L A113
H
H
H
R B4
H
O
L A114
H
H
H
R B5
H
O
L A115
H
H
H
R A2
H
O
L A116
H
H
H
R A22
H
O
L A117
H
H
H
R A28
H
O
L A118
H
H
H
R B1
H
Si(CH 3 ) 2
L A119
H
H
H
R B2
H
Si(CH 3 ) 2
L A120
H
H
H
R B3
H
Si(CH 3 ) 2
L A121
H
H
H
R B4
H
Si(CH 3 ) 2
L A122
H
H
H
R B5
H
Si(CH 3 ) 2
L A123
H
H
H
R A2
H
Si(CH 3 ) 2
L A124
H
H
H
R A22
H
Si(CH 3 ) 2
L A125
H
H
H
R A28
H
Si(CH 3 ) 2
L A126
H
H
H
H
R B1
C(CH 3 ) 2
L A127
H
H
H
H
R B2
C(CH 3 ) 2
L A128
H
H
H
H
R B3
C(CH 3 ) 2
L A129
H
H
H
H
R B4
C(CH 3 ) 2
L A130
H
H
H
H
R B5
C(CH 3 ) 2
L A131
H
H
H
H
R A2
C(CH 3 ) 2
L A132
H
H
H
H
R A22
C(CH 3 ) 2
L A133
H
H
H
H
R A28
C(CH 3 ) 2
L A134
H
H
H
H
R B1
NCH 3
L A135
H
H
H
H
R B2
NCH 3
L A136
H
H
H
H
R B3
NCH 3
L A137
H
H
H
H
R B4
NCH 3
L A138
H
H
H
H
R B5
NCH 3
L A139
H
H
H
H
R A2
NCH 3
L A140
H
H
H
H
R A22
NCH 3
L A141
H
H
H
H
R A28
NCH 3
L A142
H
H
H
H
R B1
S
L A143
H
H
H
H
R B2
S
L A144
H
H
H
H
R B3
S
L A145
H
H
H
H
R B4
S
L A146
H
H
H
H
R B5
S
L A147
H
H
H
H
R A2
S
L A148
H
H
H
H
R A22
S
L A149
H
H
H
H
R A28
S
L A150
H
H
H
H
R B1
O
L A151
H
H
H
H
R B2
O
L A152
H
H
H
H
R B3
O
L A153
H
H
H
H
R B4
O
L A154
H
H
H
H
R B5
O
L A155
H
H
H
H
R A2
O
L A156
H
H
H
H
R A22
O
L A157
H
H
H
H
R A28
O
L A158
H
H
H
H
R B1
Si(CH 3 ) 2
L A159
H
H
H
H
R B2
Si(CH 3 ) 2
L A160
H
H
H
H
R B3
Si(CH 3 ) 2
L A161
H
H
H
H
R B4
Si(CH 3 ) 2
L A162
H
H
H
H
R B5
Si(CH 3 ) 2
L A163
H
H
H
H
R A2
Si(CH 3 ) 2
L A164
H
H
H
H
R A22
Si(CH 3 ) 2
L A165
H
H
H
H
R A28
Si(CH 3 ) 2
L A331 to L A455 and L A581 to L A705 based on the following formula:
R A
R B
R C
R D
R F
R G
Y
L A331
H
H
H
H
H
H
C(CH 3 ) 2
L A332
H
R B1
H
H
H
H
C(CH 3 ) 2
L A333
H
R B2
H
H
H
H
C(CH 3 ) 2
L A334
H
R B3
H
H
H
H
C(CH 3 ) 2
L A335
H
R B4
H
H
H
H
C(CH 3 ) 2
L A336
H
R B5
H
H
H
H
C(CH 3 ) 2
L A337
H
R A2
H
H
H
H
C(CH 3 ) 2
L A338
H
R A22
H
H
H
H
C(CH 3 ) 2
L A339
H
R A28
H
H
H
H
C(CH 3 ) 2
L A340
H
H
H
H
H
H
NCH 3
L A341
H
R B1
H
H
H
H
NCH 3
L A342
H
R B2
H
H
H
H
NCH 3
L A343
H
R B3
H
H
H
H
NCH 3
L A344
H
R B4
H
H
H
H
NCH 3
L A345
H
R B5
H
H
H
H
NCH 3
L A346
H
R A2
H
H
H
H
NCH 3
L A347
H
R A22
H
H
H
H
NCH 3
L A348
H
R A28
H
H
H
H
NCH 3
L A349
H
H
H
H
H
H
S
L A350
H
R B1
H
H
H
H
S
L A351
H
R B2
H
H
H
H
S
L A352
H
R B3
H
H
H
H
S
L A353
H
R B4
H
H
H
H
S
L A354
H
R B5
H
H
H
H
S
L A355
H
R A2
H
H
H
H
S
L A356
H
R A22
H
H
H
H
S
L A357
H
R A28
H
H
H
H
S
L A358
H
H
H
H
H
H
O
L A359
H
R B1
H
H
H
H
O
L A360
H
R B2
H
H
H
H
O
L A361
H
R B3
H
H
H
H
O
L A362
H
R B4
H
H
H
H
O
L A363
H
R B5
H
H
H
H
O
L A364
H
R A2
H
H
H
H
O
L A365
H
R A22
H
H
H
H
O
L A366
H
R A28
H
H
H
H
O
L A367
H
H
H
H
H
H
Si(CH 3 ) 2
L A368
H
R B1
H
H
H
H
Si(CH 3 ) 2
L A369
H
R B2
H
H
H
H
Si(CH 3 ) 2
L A370
H
R B3
H
H
H
H
Si(CH 3 ) 2
L A371
H
R B4
H
H
H
H
Si(CH 3 ) 2
L A372
H
R B5
H
H
H
H
Si(CH 3 ) 2
L A373
H
R A2
H
H
H
H
Si(CH 3 ) 2
L A374
H
R A22
H
H
H
H
Si(CH 3 ) 2
L A375
H
R A28
H
H
H
H
Si(CH 3 ) 2
L A376
H
H
R B1
H
H
H
C(CH 3 ) 2
L A377
H
H
R B2
H
H
H
C(CH 3 ) 2
L A378
H
H
R B3
H
H
H
C(CH 3 ) 2
L A379
H
H
R B4
H
H
H
C(CH 3 ) 2
L A380
H
H
R B5
H
H
H
C(CH 3 ) 2
L A381
H
H
R A2
H
H
H
C(CH 3 ) 2
L A382
H
H
R A22
H
H
H
C(CH 3 ) 2
L A383
H
H
R A28
H
H
H
C(CH 3 ) 2
L A384
H
H
R B1
H
H
H
NCH 3
L A385
H
H
R B2
H
H
H
NCH 3
L A386
H
H
R B3
H
H
H
NCH 3
L A387
H
H
R B4
H
H
H
NCH 3
L A388
H
H
R B5
H
H
H
NCH 3
L A389
H
H
R A2
H
H
H
NCH 3
L A390
H
H
R A22
H
H
H
NCH 3
L A391
H
H
R A28
H
H
H
NCH 3
L A392
H
H
R B1
H
H
H
S
L A393
H
H
R B2
H
H
H
S
L A394
H
H
R B3
H
H
H
S
L A395
H
H
R B4
H
H
H
S
L A396
H
H
R B5
H
H
H
S
L A397
H
H
R A2
H
H
H
S
L A398
H
H
R A22
H
H
H
S
L A399
H
H
R A28
H
H
H
S
L A400
H
H
R B1
H
H
H
O
L A401
H
H
R B2
H
H
H
O
L A402
H
H
R B3
H
H
H
O
L A403
H
H
R B4
H
H
H
O
L A404
H
H
R B5
H
H
H
O
L A405
H
H
R A2
H
H
H
O
L A406
H
H
R A22
H
H
H
O
L A407
H
H
R A28
H
H
H
O
L A408
H
H
R B1
H
H
H
Si(CH 3 ) 2
L A409
H
H
R B2
H
H
H
Si(CH 3 ) 2
L A410
H
H
R B3
H
H
H
Si(CH 3 ) 2
L A411
H
H
R B4
H
H
H
Si(CH 3 ) 2
L A412
H
H
R B5
H
H
H
Si(CH 3 ) 2
L A413
H
H
R A2
H
H
H
Si(CH 3 ) 2
L A414
H
H
R A22
H
H
H
Si(CH 3 ) 2
L A415
H
H
R A28
H
H
H
Si(CH 3 ) 2
L A416
H
H
H
R B1
H
H
C(CH 3 ) 2
L A417
H
H
H
R B2
H
H
C(CH 3 ) 2
L A418
H
H
H
R B3
H
H
C(CH 3 ) 2
L A419
H
H
H
R B4
H
H
C(CH 3 ) 2
L A420
H
H
H
R B5
H
H
C(CH 3 ) 2
L A421
H
H
H
R A2
H
H
C(CH 3 ) 2
L A422
H
H
H
R A22
H
H
C(CH 3 ) 2
L A423
H
H
H
R A28
H
H
C(CH 3 ) 2
L A424
H
H
H
R B1
H
H
NCH 3
L A425
H
H
H
R B2
H
H
NCH 3
L A426
H
H
H
R B3
H
H
NCH 3
L A427
H
H
H
R B4
H
H
NCH 3
L A428
H
H
H
R B5
H
H
NCH 3
L A429
H
H
H
R A2
H
H
NCH 3
L A430
H
H
H
R A22
H
H
NCH 3
L A431
H
H
H
R A28
H
H
NCH 3
L A432
H
H
H
R B1
H
H
S
L A433
H
H
H
R B2
H
H
S
L A434
H
H
H
R B3
H
H
S
L A435
H
H
H
R B4
H
H
S
L A436
H
H
H
R B5
H
H
S
L A437
H
H
H
R A2
H
H
S
L A438
H
H
H
R A22
H
H
S
L A439
H
H
H
R A28
H
H
S
L A440
H
H
H
R B1
H
H
O
L A441
H
H
H
R B2
H
H
O
L A442
H
H
H
R B3
H
H
O
L A443
H
H
H
R B4
H
H
O
L A444
H
H
H
R B5
H
H
O
L A445
H
H
H
R A2
H
H
O
L A446
H
H
H
R A22
H
H
O
L A447
H
H
H
R A28
H
H
O
L A448
H
H
H
R B1
H
H
Si(CH 3 ) 2
L A449
H
H
H
R B2
H
H
Si(CH 3 ) 2
L A450
H
H
H
R B3
H
H
Si(CH 3 ) 2
L A451
H
H
H
R B4
H
H
Si(CH 3 ) 2
L A452
H
H
H
R B5
H
H
Si(CH 3 ) 2
L A453
H
H
H
R A2
H
H
Si(CH 3 ) 2
L A454
H
H
H
R A22
H
H
Si(CH 3 ) 2
L A455
H
H
H
R A28
H
H
Si(CH 3 ) 2
L A581
H
H
H
H
H
CH 3
C(CH 3 ) 2
L A582
H
R B1
H
H
H
CH 3
C(CH 3 ) 2
L A583
H
R B2
H
H
H
CH 3
C(CH 3 ) 2
L A584
H
R B3
H
H
H
CH 3
C(CH 3 ) 2
L A585
H
R B4
H
H
H
CH 3
C(CH 3 ) 2
L A586
H
R B5
H
H
H
CH 3
C(CH 3 ) 2
L A587
H
R A2
H
H
H
CH 3
C(CH 3 ) 2
L A588
H
R A22
H
H
H
CH 3
C(CH 3 ) 2
L A589
H
R A28
H
H
H
CH 3
C(CH 3 ) 2
L A590
H
H
H
H
H
CH 3
NCH 3
L A591
H
R B1
H
H
H
CH 3
NCH 3
L A592
H
R B2
H
H
H
CH 3
NCH 3
L A593
H
R B3
H
H
H
CH 3
NCH 3
L A594
H
R B4
H
H
H
CH 3
NCH 3
L A595
H
R B5
H
H
H
CH 3
NCH 3
L A596
H
R A2
H
H
H
CH 3
NCH 3
L A597
H
R A22
H
H
H
CH 3
NCH 3
L A598
H
R A28
H
H
H
CH 3
NCH 3
L A599
H
H
H
H
H
CH 3
S
L A600
H
R B1
H
H
H
CH 3
S
L A601
H
R B2
H
H
H
CH 3
S
L A602
H
R B3
H
H
H
CH 3
S
L A603
H
R B4
H
H
H
CH 3
S
L A604
H
R B5
H
H
H
CH 3
S
L A605
H
R A2
H
H
H
CH 3
S
L A606
H
R A22
H
H
H
CH 3
S
L A607
H
R A28
H
H
H
CH 3
S
L A608
H
H
H
H
H
CH 3
O
L A609
H
R B1
H
H
H
CH 3
O
L A610
H
R B2
H
H
H
CH 3
O
L A611
H
R B3
H
H
H
CH 3
O
L A612
H
R B4
H
H
H
CH 3
O
L A613
H
R B5
H
H
H
CH 3
O
L A614
H
R A2
H
H
H
CH 3
O
L A615
H
R A22
H
H
H
CH 3
O
L A616
H
R A28
H
H
H
CH 3
O
L A617
H
H
H
H
H
CH 3
Si(CH 3 ) 2
L A618
H
R B1
H
H
H
CH 3
Si(CH 3 ) 2
L A619
H
R B2
H
H
H
CH 3
Si(CH 3 ) 2
L A620
H
R B3
H
H
H
CH 3
Si(CH 3 ) 2
L A621
H
R B4
H
H
H
CH 3
Si(CH 3 ) 2
L A622
H
R B5
H
H
H
CH 3
Si(CH 3 ) 2
L A623
H
R A2
H
H
H
CH 3
Si(CH 3 ) 2
L A624
H
R A22
H
H
H
CH 3
Si(CH 3 ) 2
L A625
H
R A28
H
H
H
CH 3
Si(CH 3 ) 2
L A626
H
H
R B1
H
H
CH 3
C(CH 3 ) 2
L A627
H
H
R B2
H
H
CH 3
C(CH 3 ) 2
L A628
H
H
R B3
H
H
CH 3
C(CH 3 ) 2
L A629
H
H
R B4
H
H
CH 3
C(CH 3 ) 2
L A630
H
H
R B5
H
H
CH 3
C(CH 3 ) 2
L A631
H
H
R A2
H
H
CH 3
C(CH 3 ) 2
L A632
H
H
R A22
H
H
CH 3
C(CH 3 ) 2
L A633
H
H
R A28
H
H
CH 3
C(CH 3 ) 2
L A634
H
H
R B1
H
H
CH 3
NCH 3
L A635
H
H
R B2
H
H
CH 3
NCH 3
L A636
H
H
R B3
H
H
CH 3
NCH 3
L A637
H
H
R B4
H
H
CH 3
NCH 3
L A638
H
H
R B5
H
H
CH 3
NCH 3
L A639
H
H
R A2
H
H
CH 3
NCH 3
L A640
H
H
R A22
H
H
CH 3
NCH 3
L A641
H
H
R A28
H
H
CH 3
NCH 3
L A642
H
H
R B1
H
H
CH 3
S
L A643
H
H
R B2
H
H
CH 3
S
L A644
H
H
R B3
H
H
CH 3
S
L A645
H
H
R B4
H
H
CH 3
S
L A646
H
H
R B5
H
H
CH 3
S
L A647
H
H
R A2
H
H
CH 3
S
L A648
H
H
R A22
H
H
CH 3
S
L A649
H
H
R A28
H
H
CH 3
S
L A650
H
H
R B1
H
H
CH 3
O
L A651
H
H
R B2
H
H
CH 3
O
L A652
H
H
R B3
H
H
CH 3
O
L A653
H
H
R B4
H
H
CH 3
O
L A654
H
H
R B5
H
H
CH 3
O
L A655
H
H
R A2
H
H
CH 3
O
L A656
H
H
R A22
H
H
CH 3
O
L A657
H
H
R A28
H
H
CH 3
O
L A658
H
H
R B1
H
H
CH 3
Si(CH 3 ) 2
L A659
H
H
R B2
H
H
CH 3
Si(CH 3 ) 2
L A660
H
H
R B3
H
H
CH 3
Si(CH 3 ) 2
L A661
H
H
R B4
H
H
CH 3
Si(CH 3 ) 2
L A662
H
H
R B5
H
H
CH 3
Si(CH 3 ) 2
L A663
H
H
R A2
H
H
CH 3
Si(CH 3 ) 2
L A664
H
H
R A22
H
H
CH 3
Si(CH 3 ) 2
L A665
H
H
R A28
H
H
CH 3
Si(CH 3 ) 2
L A666
H
H
H
R B1
H
CH 3
C(CH 3 ) 2
L A667
H
H
H
R B2
H
CH 3
C(CH 3 ) 2
L A668
H
H
H
R B3
H
CH 3
C(CH 3 ) 2
L A669
H
H
H
R B4
H
CH 3
C(CH 3 ) 2
L A670
H
H
H
R B5
H
CH 3
C(CH 3 ) 2
L A671
H
H
H
R A2
H
CH 3
C(CH 3 ) 2
L A672
H
H
H
R A22
H
CH 3
C(CH 3 ) 2
L A673
H
H
H
R A28
H
CH 3
C(CH 3 ) 2
L A674
H
H
H
R B1
H
CH 3
NCH 3
L A675
H
H
H
R B2
H
CH 3
NCH 3
L A676
H
H
H
R B3
H
CH 3
NCH 3
L A677
H
H
H
R B4
H
CH 3
NCH 3
L A678
H
H
H
R B5
H
CH 3
NCH 3
L A679
H
H
H
R A2
H
CH 3
NCH 3
L A680
H
H
H
R A22
H
CH 3
NCH 3
L A681
H
H
H
R A28
H
CH 3
NCH 3
L A682
H
H
H
R B1
H
CH 3
S
L A683
H
H
H
R B2
H
CH 3
S
L A684
H
H
H
R B3
H
CH 3
S
L A685
H
H
H
R B4
H
CH 3
S
L A686
H
H
H
R B5
H
CH 3
S
L A687
H
H
H
R A2
H
CH 3
S
L A688
H
H
H
R A22
H
CH 3
S
L A689
H
H
H
R A28
H
CH 3
S
L A690
H
H
H
R B1
H
CH 3
O
L A691
H
H
H
R B2
H
CH 3
O
L A692
H
H
H
R B3
H
CH 3
O
L A693
H
H
H
R B4
H
CH 3
O
L A694
H
H
H
R B5
H
CH 3
O
L A695
H
H
H
R A2
H
CH 3
O
L A696
H
H
H
R A22
H
CH 3
O
L A697
H
H
H
R A28
H
CH 3
O
L A698
H
H
H
R B1
H
CH 3
Si(CH 3 ) 2
L A699
H
H
H
R B2
H
CH 3
Si(CH 3 ) 2
L A700
H
H
H
R B3
H
CH 3
Si(CH 3 ) 2
L A701
H
H
H
R B4
H
CH 3
Si(CH 3 ) 2
L A702
H
H
H
R B5
H
CH 3
Si(CH 3 ) 2
L A703
H
H
H
R A2
H
CH 3
Si(CH 3 ) 2
L A704
H
H
H
R A22
H
CH 3
Si(CH 3 ) 2
L A705
H
H
H
R A28
H
CH 3
Si(CH 3 ) 2
L A1331 to L A1455 and L A1581 to L A1705 based on the following formula:
R A
R B
R C
R E
R F
R G
Y
L A1331
H
H
H
H
H
H
C(CH 3 ) 2
L A1332
H
R B1
H
H
H
H
C(CH 3 ) 2
L A1333
H
R B2
H
H
H
H
C(CH 3 ) 2
L A1334
H
R B3
H
H
H
H
C(CH 3 ) 2
L A1335
H
R B4
H
H
H
H
C(CH 3 ) 2
L A1336
H
R B5
H
H
H
H
C(CH 3 ) 2
L A1337
H
R A2
H
H
H
H
C(CH 3 ) 2
L A1338
H
R A22
H
H
H
H
C(CH 3 ) 2
L A1339
H
R A28
H
H
H
H
C(CH 3 ) 2
L A1340
H
H
H
H
H
H
NCH 3
L A1341
H
R B1
H
H
H
H
NCH 3
L A1342
H
R B2
H
H
H
H
NCH 3
L A1343
H
R B3
H
H
H
H
NCH 3
L A1344
H
R B4
H
H
H
H
NCH 3
L A1345
H
R B5
H
H
H
H
NCH 3
L A1346
H
R A2
H
H
H
H
NCH 3
L A1347
H
R A22
H
H
H
H
NCH 3
L A1348
H
R A28
H
H
H
H
NCH 3
L A1349
H
H
H
H
H
H
S
L A1350
H
R B1
H
H
H
H
S
L A1351
H
R B2
H
H
H
H
S
L A1352
H
R B3
H
H
H
H
S
L A1353
H
R B4
H
H
H
H
S
L A1354
H
R B5
H
H
H
H
S
L A1355
H
R A2
H
H
H
H
S
L A1356
H
R A22
H
H
H
H
S
L A1357
H
R A28
H
H
H
H
S
L A1358
H
H
H
H
H
H
O
L A1359
H
R B1
H
H
H
H
O
L A1360
H
R B2
H
H
H
H
O
L A1361
H
R B3
H
H
H
H
O
L A1362
H
R B4
H
H
H
H
O
L A1363
H
R B5
H
H
H
H
O
L A1364
H
R A2
H
H
H
H
O
L A1365
H
R A22
H
H
H
H
O
L A1366
H
R A28
H
H
H
H
O
L A1367
H
H
H
H
H
H
Si(CH 3 ) 2
L A1368
H
R B1
H
H
H
H
Si(CH 3 ) 2
L A1369
H
R B2
H
H
H
H
Si(CH 3 ) 2
L A1370
H
R B3
H
H
H
H
Si(CH 3 ) 2
L A1371
H
R B4
H
H
H
H
Si(CH 3 ) 2
L A1372
H
R B5
H
H
H
H
Si(CH 3 ) 2
L A1373
H
R A2
H
H
H
H
Si(CH 3 ) 2
L A1374
H
R A22
H
H
H
H
Si(CH 3 ) 2
L A1375
H
R A28
H
H
H
H
Si(CH 3 ) 2
L A1376
H
H
R B1
H
H
H
C(CH 3 ) 2
L A1377
H
H
R B2
H
H
H
C(CH 3 ) 2
L A1378
H
H
R B3
H
H
H
C(CH 3 ) 2
L A1379
H
H
R B4
H
H
H
C(CH 3 ) 2
L A1380
H
H
R B5
H
H
H
C(CH 3 ) 2
L A1381
H
H
R A2
H
H
H
C(CH 3 ) 2
L A1382
H
H
R A22
H
H
H
C(CH 3 ) 2
L A1383
H
H
R A28
H
H
H
C(CH 3 ) 2
L A1384
H
H
R B1
H
H
H
NCH 3
L A1385
H
H
R B2
H
H
H
NCH 3
L A1386
H
H
R B3
H
H
H
NCH 3
L A1387
H
H
R B4
H
H
H
NCH 3
L A1388
H
H
R B5
H
H
H
NCH 3
L A1389
H
H
R A2
H
H
H
NCH 3
L A1390
H
H
R A22
H
H
H
NCH 3
L A1391
H
H
R A28
H
H
H
NCH 3
L A1392
H
H
R B1
H
H
H
S
L A1393
H
H
R B2
H
H
H
S
L A1394
H
H
R B3
H
H
H
S
L A1395
H
H
R B4
H
H
H
S
L A1396
H
H
R B5
H
H
H
S
L A1397
H
H
R A2
H
H
H
S
L A1398
H
H
R A22
H
H
H
S
L A1399
H
H
R A28
H
H
H
S
L A1400
H
H
R B1
H
H
H
O
L A1401
H
H
R B2
H
H
H
O
L A1402
H
H
R B3
H
H
H
O
L A1403
H
H
R B4
H
H
H
O
L A1404
H
H
R B5
H
H
H
O
L A1405
H
H
R A2
H
H
H
O
L A1406
H
H
R A22
H
H
H
O
L A1407
H
H
R A28
H
H
H
O
L A1408
H
H
R B1
H
H
H
Si(CH 3 ) 2
L A1409
H
H
R B2
H
H
H
Si(CH 3 ) 2
L A1410
H
H
R B3
H
H
H
Si(CH 3 ) 2
L A1411
H
H
R B4
H
H
H
Si(CH 3 ) 2
L A1412
H
H
R B5
H
H
H
Si(CH 3 ) 2
L A1413
H
H
R A2
H
H
H
Si(CH 3 ) 2
L A1414
H
H
R A22
H
H
H
Si(CH 3 ) 2
L A1415
H
H
R A28
H
H
H
Si(CH 3 ) 2
L A1416
H
H
H
R B1
H
H
C(CH 3 ) 2
L A1417
H
H
H
R B2
H
H
C(CH 3 ) 2
L A1418
H
H
H
R B3
H
H
C(CH 3 ) 2
L A1419
H
H
H
R B4
H
H
C(CH 3 ) 2
L A1420
H
H
H
R B5
H
H
C(CH 3 ) 2
L A1421
H
H
H
R A2
H
H
C(CH 3 ) 2
L A1422
H
H
H
R A22
H
H
C(CH 3 ) 2
L A1423
H
H
H
R A28
H
H
C(CH 3 ) 2
L A1424
H
H
H
R B1
H
H
NCH 3
L A1425
H
H
H
R B2
H
H
NCH 3
L A1426
H
H
H
R B3
H
H
NCH 3
L A1427
H
H
H
R B4
H
H
NCH 3
L A1428
H
H
H
R B5
H
H
NCH 3
L A1429
H
H
H
R A2
H
H
NCH 3
L A1430
H
H
H
R A22
H
H
NCH 3
L A1431
H
H
H
R A28
H
H
NCH 3
L A1432
H
H
H
R B1
H
H
S
L A1433
H
H
H
R B2
H
H
S
L A1434
H
H
H
R B3
H
H
S
L A1435
H
H
H
R B4
H
H
S
L A1436
H
H
H
R B5
H
H
S
L A1437
H
H
H
R A2
H
H
S
L A1438
H
H
H
R A22
H
H
S
L A1439
H
H
H
R A28
H
H
S
L A1440
H
H
H
R B1
H
H
O
L A1441
H
H
H
R B2
H
H
O
L A1442
H
H
H
R B3
H
H
O
L A1443
H
H
H
R B4
H
H
O
L A1444
H
H
H
R B5
H
H
O
L A1445
H
H
H
R A2
H
H
O
L A1446
H
H
H
R A22
H
H
O
L A1447
H
H
H
R A28
H
H
O
L A1448
H
H
H
R B1
H
H
Si(CH 3 ) 2
L A1449
H
H
H
R B2
H
H
Si(CH 3 ) 2
L A1450
H
H
H
R B3
H
H
Si(CH 3 ) 2
L A1451
H
H
H
R B4
H
H
Si(CH 3 ) 2
L A1452
H
H
H
R B5
H
H
Si(CH 3 ) 2
L A1453
H
H
H
R A2
H
H
Si(CH 3 ) 2
L A1454
H
H
H
R A22
H
H
Si(CH 3 ) 2
L A1455
H
H
H
R A28
H
H
Si(CH 3 ) 2
L A1581
H
H
H
H
H
CH 3
C(CH 3 ) 2
L A1582
H
R B1
H
H
H
CH 3
C(CH 3 ) 2
L A1583
H
R B2
H
H
H
CH 3
C(CH 3 ) 2
L A1584
H
R B3
H
H
H
CH 3
C(CH 3 ) 2
L A1585
H
R B4
H
H
H
CH 3
C(CH 3 ) 2
L A1586
H
R B5
H
H
H
CH 3
C(CH 3 ) 2
L A1587
H
R A2
H
H
H
CH 3
C(CH 3 ) 2
L A1588
H
R A22
H
H
H
CH 3
C(CH 3 ) 2
L A1589
H
R A28
H
H
H
CH 3
C(CH 3 ) 2
L A1590
H
H
H
H
H
CH 3
NCH 3
L A1591
H
R B1
H
H
H
CH 3
NCH 3
L A1592
H
R B2
H
H
H
CH 3
NCH 3
L A1593
H
R B3
H
H
H
CH 3
NCH 3
L A1594
H
R B4
H
H
H
CH 3
NCH 3
L A1595
H
R B5
H
H
H
CH 3
NCH 3
L A1596
H
R A2
H
H
H
CH 3
NCH 3
L A1597
H
R A22
H
H
H
CH 3
NCH 3
L A1598
H
R A28
H
H
H
CH 3
NCH 3
L A1599
H
H
H
H
H
CH 3
S
L A1600
H
R B1
H
H
H
CH 3
S
L A1601
H
R B2
H
H
H
CH 3
S
L A1602
H
R B3
H
H
H
CH 3
S
L A1603
H
R B4
H
H
H
CH 3
S
L A1604
H
R B5
H
H
H
CH 3
S
L A1605
H
R A2
H
H
H
CH 3
S
L A1606
H
R A22
H
H
H
CH 3
S
L A1607
H
R A28
H
H
H
CH 3
S
L A1608
H
H
H
H
H
CH 3
O
L A1609
H
R B1
H
H
H
CH 3
O
L A1610
H
R B2
H
H
H
CH 3
O
L A1611
H
R B3
H
H
H
CH 3
O
L A1612
H
R B4
H
H
H
CH 3
O
L A1613
H
R B5
H
H
H
CH 3
O
L A1614
H
R A2
H
H
H
CH 3
O
L A1615
H
R A22
H
H
H
CH 3
O
L A1616
H
R A28
H
H
H
CH 3
O
L A1617
H
H
H
H
H
CH 3
Si(CH 3 ) 2
L A1618
H
R B1
H
H
H
CH 3
Si(CH 3 ) 2
L A1619
H
R B2
H
H
H
CH 3
Si(CH 3 ) 2
L A1620
H
R B3
H
H
H
CH 3
Si(CH 3 ) 2
L A1621
H
R B4
H
H
H
CH 3
Si(CH 3 ) 2
L A1622
H
R B5
H
H
H
CH 3
Si(CH 3 ) 2
L A1623
H
R A2
H
H
H
CH 3
Si(CH 3 ) 2
L A1624
H
R A22
H
H
H
CH 3
Si(CH 3 ) 2
L A1625
H
R A28
H
H
H
CH 3
Si(CH 3 ) 2
L A1626
H
H
R B1
H
H
CH 3
C(CH 3 ) 2
L A1627
H
H
R B2
H
H
CH 3
C(CH 3 ) 2
L A1628
H
H
R B3
H
H
CH 3
C(CH 3 ) 2
L A1629
H
H
R B4
H
H
CH 3
C(CH 3 ) 2
L A1630
H
H
R B5
H
H
CH 3
C(CH 3 ) 2
L A1631
H
H
R A2
H
H
CH 3
C(CH 3 ) 2
L A1632
H
H
R A22
H
H
CH 3
C(CH 3 ) 2
L A1633
H
H
R A28
H
H
CH 3
C(CH 3 ) 2
L A1634
H
H
R B1
H
H
CH 3
NCH 3
L A1635
H
H
R B2
H
H
CH 3
NCH 3
L A1636
H
H
R B3
H
H
CH 3
NCH 3
L A1637
H
H
R B4
H
H
CH 3
NCH 3
L A1638
H
H
R B5
H
H
CH 3
NCH 3
L A1639
H
H
R A2
H
H
CH 3
NCH 3
L A1640
H
H
R A22
H
H
CH 3
NCH 3
L A1641
H
H
R A28
H
H
CH 3
NCH 3
L A1642
H
H
R B1
H
H
CH 3
NCH 3
L A1643
H
H
R B2
H
H
CH 3
S
L A1644
H
H
R B3
H
H
CH 3
S
L A1645
H
H
R B4
H
H
CH 3
S
L A1646
H
H
R B5
H
H
CH 3
S
L A1647
H
H
R A2
H
H
CH 3
S
L A1648
H
H
R A22
H
H
CH 3
S
L A1649
H
H
R A28
H
H
CH 3
S
L A1650
H
H
R B1
H
H
CH 3
O
L A1651
H
H
R B2
H
H
CH 3
O
L A1652
H
H
R B3
H
H
CH 3
O
L A1653
H
H
R B4
H
H
CH 3
O
L A1654
H
H
R B5
H
H
CH 3
O
L A1655
H
H
R A2
H
H
CH 3
O
L A1656
H
H
R A22
H
H
CH 3
O
L A1657
H
H
R A28
H
H
CH 3
O
L A1658
H
H
R B1
H
H
CH 3
Si(CH 3 ) 2
L A1659
H
H
R B2
H
H
CH 3
Si(CH 3 ) 2
L A1660
H
H
R B3
H
H
CH 3
Si(CH 3 ) 2
L A1661
H
H
R B4
H
H
CH 3
Si(CH 3 ) 2
L A1662
H
H
R B5
H
H
CH 3
Si(CH 3 ) 2
L A1663
H
H
R A2
H
H
CH 3
Si(CH 3 ) 2
L A1664
H
H
R A22
H
H
CH 3
Si(CH 3 ) 2
L A1665
H
H
R A28
H
H
CH 3
Si(CH 3 ) 2
L A1666
H
H
H
R B1
H
CH 3
C(CH 3 ) 2
L A1667
H
H
H
R B2
H
CH 3
C(CH 3 ) 2
L A1668
H
H
H
R B3
H
CH 3
C(CH 3 ) 2
L A1669
H
H
H
R B4
H
CH 3
C(CH 3 ) 2
L A1670
H
H
H
R B5
H
CH 3
C(CH 3 ) 2
L A1671
H
H
H
R A2
H
CH 3
C(CH 3 ) 2
L A1672
H
H
H
R A22
H
CH 3
C(CH 3 ) 2
L A1673
H
H
H
R A28
H
CH 3
C(CH 3 ) 2
L A1674
H
H
H
R B1
H
CH 3
NCH 3
L A1675
H
H
H
R B2
H
CH 3
NCH 3
L A1676
H
H
H
R B3
H
CH 3
NCH 3
L A1677
H
H
H
R B4
H
CH 3
NCH 3
L A1678
H
H
H
R B5
H
CH 3
NCH 3
L A1679
H
H
H
R A2
H
CH 3
NCH 3
L A1680
H
H
H
R A22
H
CH 3
NCH 3
L A1681
H
H
H
R A28
H
CH 3
NCH 3
L A1682
H
H
H
R B1
H
CH 3
S
L A1683
H
H
H
R B2
H
CH 3
S
L A1684
H
H
H
R B3
H
CH 3
S
L A1685
H
H
H
R B4
H
CH 3
S
L A1686
H
H
H
R B5
H
CH 3
S
L A1687
H
H
H
R A2
H
CH 3
S
L A1688
H
H
H
R A22
H
CH 3
S
L A1689
H
H
H
R A28
H
CH 3
S
L A1690
H
H
H
R B1
H
CH 3
O
L A1691
H
H
H
R B2
H
CH 3
O
L A1692
H
H
H
R B3
H
CH 3
O
L A1693
H
H
H
R B4
H
CH 3
O
L A1694
H
H
H
R B5
H
CH 3
O
L A1695
H
H
H
R A2
H
CH 3
O
L A1696
H
H
H
R A22
H
CH 3
O
L A1697
H
H
H
R A28
H
CH 3
O
L A1698
H
H
H
R B1
H
CH 3
Si(CH 3 ) 2
L A1699
H
H
H
R B2
H
CH 3
Si(CH 3 ) 2
L A1700
H
H
H
R B3
H
CH 3
Si(CH 3 ) 2
L A1701
H
H
H
R B4
H
CH 3
Si(CH 3 ) 2
L A1702
H
H
H
R B5
H
CH 3
Si(CH 3 ) 2
L A1703
H
H
H
R A2
H
CH 3
Si(CH 3 ) 2
L A1704
H
H
H
R A22
H
CH 3
Si(CH 3 ) 2
L A1705
H
H
H
R A28
H
CH 3
Si(CH 3 ) 2
wherein R A2 , R A22 , and R A28 have the following structures:
and
wherein R B1 to R B5 have the following structures:
11. The compound of claim 1 , wherein ligand L B is selected from the group consisting of:
wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d 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, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.
12. The compound of claim 1 , wherein ligand L B is selected from the group consisting of:
13. The compound of claim 1 , wherein ligand L C is selected from the group consisting of:
14. The compound of claim 10 , wherein the compound is Compound x having the formula M(L Ai ) 2 (L Cj );
wherein x=13(i−1)+j, i is an integer from 1 to 830 or 1331 to 1830, and j is an integer from 1 to 13; and
wherein L Cj has one of the following formula:
15. 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 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 X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are each independently a CR or N;
wherein X 7 is CH;
wherein X 8 is carbon or nitrogen;
wherein when X 6 is a CR, R is hydrogen;
wherein Y is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R CC , and R DD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein each of R, R′, R″, R CC , and R DD 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 each of R X , R Y , and R Z are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein each of R X , R Y , and R Z do not comprise alkenyl;
wherein when X 1 to X 5 is carbon, then R 1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof; and when R 1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
wherein when at least one of X 1 to X 5 is nitrogen, then R 1 is 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 R 1 , R, R′, R″, R CC , R DD , R X , R Y , and R Z are optionally joined or fused into a ring.
16. The OLED of claim 15 , wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.
17. The OLED 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 OLED of claim 15 , 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.
19. A formulation comprising a compound 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 X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are each independently a CR or N;
wherein X 7 is CH;
wherein X 8 is carbon or nitrogen;
wherein when X 6 is a CR, R is hydrogen;
wherein Y is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R CC , and R DD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein each of R, R′, R″, R CC , and R DD 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 each of R X , R Y , and R Z are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein each of R X , R Y , and R Z do not comprise alkenyl;
wherein when X 1 to X 5 is carbon, then R 1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof; and when R 1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
wherein when at least one of X 1 to X 5 is nitrogen, then R 1 is 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 1 , R, R′, R″, R CC , R DD , R X , R Y , and R Z are optionally joined or fused into a ring.
20. A compound of claim 1 , wherein the ligand L B is selected from the group consisting of:
wherein in ligand L B :
X 1 to X 13 are each independently selected from the group consisting of carbon and nitrogen;
R a , R b , R c , and R d may each represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein any adjacent substituents of R a , R b , R c , R d , do not join or fuse to form a ring;
wherein x is 1 or 2;
wherein y is 1 or 2;
wherein z is 0 or 1; and
wherein each of R a , R b , R c , R d , 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.