USRE48809EActiveUtilityPatentIndex 62
Organic electroluminescent materials and devices
Est. expiryMay 15, 2035(~8.9 yrs left)· nominal 20-yr term from priority
H10K 2101/90C09K 2211/185C09K 11/06C07F 15/0033C09K 11/025C07D 495/04C07D 239/70C07D 487/04C07D 491/048H05B 33/14H01L 51/5016H01L 51/0061H01L 51/0052H01L 51/0073H01L 51/0074H01L 51/0055H01L 51/0085H10K 50/11H10K 85/6572H10K 85/6576H10K 85/342H10K 2101/10H10K 85/615H10K 85/636H10K 85/654H10K 85/623H10K 85/6574H10K 85/657H10K 50/12
62
PatentIndex Score
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Cited by
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References
20
Claims
Abstract
Novel ligands for metal complexes containing five-membered ring fused on pyridine or pyrimidine ring combined with partially fluorinated side chains exhibiting improved external quantum efficiency and lifetime are disclosed.
Claims
exact text as granted — not AI-modifiedWe claim:
1. A compound comprising a ligand L A of Formula I:
wherein ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R is fused to ring B and has a structure of Formula II:
wherein the wave lines indicate bonds to ring B;
wherein R 1 represents mono, di, tri, or tetra substitution, or no substitution;
wherein R 2 represents mono or di substitution, or no substitution;
wherein X 1 , X 2 , X 3 , and X 4 are each independently carbon or nitrogen;
wherein at least one of X 1 to X 4 is nitrogen;
wherein at least two adjacent of X 1 , X 2 , X 3 , and X 4 are carbon and fuse to R;
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 1 , R 2 , R 3 , R 4 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any two adjacent substituents are optionally joined to form into a ring;
wherein at least one of R 3 and R 4 comprises a chemical group selected from the group consisting of alkyl, cycloalkyl, partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;
wherein the ligand L A is coordinated to a metal M;
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.
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 the ligand L A is selected from the group consisting of:
4. The compound of claim 1 , wherein the ligand L A is:
5. The compound of claim 1 , wherein at least one of R 3 and R 4 is a chemical group selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof.
6. The compound of claim 1 , wherein R 3 and R 4 are not hydrogen.
7. The compound of claim 1 , wherein at least one of X 1 , X 2 , X 3 , and X 4 is nitrogen.
8. The compound of claim 1 , wherein at least one of R 3 and R 4 is selected from the group consisting of:
9. The compound of claim 1 , wherein R 3 and R 4 are joined to form a ring structure selected from the group consisting of:
10. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
11. The compound of claim 8 , wherein the ligand L A is selected from the group consisting of L A1 through L A750 defined as follows:
L A1 through L A375 are based on a structure of Formula IV,
in which R 3 , R 4 , and X are defined as:
Ligand
R 3
R 4
X
L A1
H
R A2
O
L A2
R A2
R A2
O
L A3
R A3
R A2
O
L A4
R A14
R A2
O
L A5
R A22
R A2
O
L A6
R A28
R A2
O
L A7
H
R A3
O
L A8
R A2
R A3
O
L A9
R A3
R A3
O
L A10
R A14
R A3
O
L A11
R A22
R A3
O
L A12
R A28
R A3
O
L A13
H
R A14
O
L A14
R A2
R A14
O
L A15
R A3
R A14
O
L A16
R A14
R A14
O
L A17
R A22
R A14
O
L A18
R A28
R A14
O
L A19
H
R A22
O
L A20
R A2
R A22
O
L A21
R A3
R A22
O
L A22
R A14
R A22
O
L A23
R A22
R A22
O
L A24
R A28
R A22
O
L A25
H
R A28
O
L A26
R A2
R A28
O
L A27
R A3
R A28
O
L A28
R A14
R A28
O
L A29
R A22
R A28
O
L A30
R A28
R A28
O
L A31
R A2
H
O
L A32
R A3
H
O
L A33
R A14
H
O
L A34
R A22
H
O
L A35
R A28
H
O
L A36
R A2
R B1
O
L A37
R A3
R B1
O
L A38
R A14
R B1
O
L A39
R A22
R B1
O
L A40
R A28
R B1
O
L A41
R A2
R B2
O
L A42
R A3
R B2
O
L A43
R A14
R B2
O
L A44
R A22
R B2
O
L A45
R A28
R B2
O
L A46
R A2
R B3
O
L A47
R A3
R B3
O
L A48
R A14
R B3
O
L A49
R A22
R B3
O
L A50
R A28
R B3
O
L A51
R A2
R B4
O
L A52
R A3
R B4
O
L A53
R A14
R B4
O
L A54
R A22
R B4
O
L A55
R A28
R B4
O
L A56
R B1
R A2
O
L A57
R B1
R A3
O
L A58
R B1
R A14
O
L A59
R B1
R A22
O
L A60
R B1
R A28
O
L A61
R B2
R A2
O
L A62
R B2
R A3
O
L A63
R B2
R A14
O
L A64
R B2
R A22
O
L A65
R B2
R A28
O
L A66
R B3
R A2
O
L A67
R B3
R A3
O
L A68
R B3
R A14
O
L A69
R B3
R A22
O
L A70
R B3
R A28
O
L A71
R B4
R A2
O
L A72
R B4
R A3
O
L A73
R B4
R A14
O
L A74
R B4
R A22
O
L A75
R B4
R A28
O
L A76
H
R A2
S
L A77
R A2
R A2
S
L A78
R A3
R A2
S
L A79
R A14
R A2
S
L A80
R A22
R A2
S
L A81
R A28
R A2
S
L A82
H
R A3
S
L A83
R A2
R A3
S
L A84
R A3
R A3
S
L A85
R A14
R A3
S
L A86
R A22
R A3
S
L A87
R A28
R A3
S
L A88
H
R A14
S
L A89
R A2
R A14
S
L A90
R A3
R A14
S
L A91
R A14
R A14
S
L A92
R A22
R A14
S
L A93
R A28
R A14
S
L A94
H
R A22
S
L A95
R A2
R A22
S
L A96
R A3
R A22
S
L A97
R A14
R A22
S
L A98
R A22
R A22
S
L A99
R A28
R A22
S
L A100
H
R A28
S
L A101
R A2
R A28
S
L A102
R A3
R A28
S
L A103
R A14
R A28
S
L A104
R A22
R A28
S
L A105
R A28
R A28
S
L A106
R A2
H
S
L A107
R A3
H
S
L A108
R A14
H
S
L A109
R A22
H
S
L A110
R A28
H
S
L A111
R A2
R B1
S
L A112
R A3
R B1
S
L A113
R A14
R B1
S
L A114
R A22
R B1
S
L A115
R A28
R B1
S
L A116
R A2
R B2
S
L A117
R A3
R B2
S
L A118
R A14
R B2
S
L A119
R A22
R B2
S
L A120
R A28
R B2
S
L A121
R A2
R B3
S
L A122
R A3
R B3
S
L A123
R A14
R B3
S
L A124
R A22
R B3
S
L A125
R A28
R B3
S
L A126
R A2
R B4
S
L A127
R A3
R B4
S
L A128
R A14
R B4
S
L A129
R A22
R B4
S
L A130
R A28
R B4
S
L A131
R B1
R A2
S
L A132
R B1
R A3
S
L A133
R B1
R A14
S
L A134
R B1
R A22
S
L A135
R B1
R A28
S
L A136
R B2
R A2
S
L A137
R B2
R A3
S
L A138
R B2
R A14
S
L A139
R B2
R A22
S
L A140
R B2
R A28
S
L A141
R B3
R A2
S
L A142
R B3
R A3
S
L A143
R B3
R A14
S
L A144
R B3
R A22
S
L A145
R B3
R A28
S
L A146
R B4
R A2
S
L A147
R B4
R A3
S
L A148
R B4
R A14
S
L A149
R B4
R A22
S
L A150
R B4
R A28
S
L A151
H
R A2
C(CH 3 ) 2
L A152
R A2
R A2
C(CH 3 ) 2
L A153
R A3
R A2
C(CH 3 ) 2
L A154
R A14
R A2
C(CH 3 ) 2
L A155
R A22
R A2
C(CH 3 ) 2
L A156
R A28
R A2
C(CH 3 ) 2
L A157
H
R A3
C(CH 3 ) 2
L A158
R A2
R A3
C(CH 3 ) 2
L A159
R A3
R A3
C(CH 3 ) 2
L A160
R A14
R A3
C(CH 3 ) 2
L A161
R A22
R A3
C(CH 3 ) 2
L A162
R A28
R A3
C(CH 3 ) 2
L A163
H
R A14
C(CH 3 ) 2
L A164
R A2
R A14
C(CH 3 ) 2
L A165
R A3
R A14
C(CH 3 ) 2
L A166
R A14
R A14
C(CH 3 ) 2
L A167
R A22
R A14
C(CH 3 ) 2
L A168
R A28
R A14
C(CH 3 ) 2
L A169
H
R A22
C(CH 3 ) 2
L A170
R A2
R A22
C(CH 3 ) 2
L A171
R A3
R A22
C(CH 3 ) 2
L A172
R A14
R A22
C(CH 3 ) 2
L A173
R A22
R A22
C(CH 3 ) 2
L A174
R A28
R A22
C(CH 3 ) 2
L A175
H
R A28
C(CH 3 ) 2
L A176
R A2
R A28
C(CH 3 ) 2
L A177
R A3
R A28
C(CH 3 ) 2
L A178
R A14
R A28
C(CH 3 ) 2
L A179
R A22
R A28
C(CH 3 ) 2
L A180
R A28
R A28
C(CH 3 ) 2
L A181
R A2
H
C(CH 3 ) 2
L A182
R A3
H
C(CH 3 ) 2
L A183
R A14
H
C(CH 3 ) 2
L A184
R A22
H
C(CH 3 ) 2
L A185
R A28
H
C(CH 3 ) 2
L A186
R A2
R B1
C(CH 3 ) 2
L A187
R A3
R B1
C(CH 3 ) 2
L A188
R A14
R B1
C(CH 3 ) 2
L A189
R A22
R B1
C(CH 3 ) 2
L A190
R A28
R B1
C(CH 3 ) 2
L A191
R A2
R B2
C(CH 3 ) 2
L A192
R A3
R B2
C(CH 3 ) 2
L A193
R A14
R B2
C(CH 3 ) 2
L A194
R A22
R B2
C(CH 3 ) 2
L A195
R A28
R B2
C(CH 3 ) 2
L A196
R A2
R B3
C(CH 3 ) 2
L A197
R A3
R B3
C(CH 3 ) 2
L A198
R A14
R B3
C(CH 3 ) 2
L A199
R A22
R B3
C(CH 3 ) 2
L A200
R A28
R B3
C(CH 3 ) 2
L A201
R A2
R B4
C(CH 3 ) 2
L A202
R A3
R B4
C(CH 3 ) 2
L A203
R A14
R B4
C(CH 3 ) 2
L A204
R A22
R B4
C(CH 3 ) 2
L A205
R A28
R B4
C(CH 3 ) 2
L A206
R B1
R A2
C(CH 3 ) 2
L A207
R B1
R A3
C(CH 3 ) 2
L A208
R B1
R A14
C(CH 3 ) 2
L A209
R B1
R A22
C(CH 3 ) 2
L A210
R B1
R A28
C(CH 3 ) 2
L A211
R B2
R A2
C(CH 3 ) 2
L A212
R B2
R A3
C(CH 3 ) 2
L A213
R B2
R A14
C(CH 3 ) 2
L A214
R B2
R A22
C(CH 3 ) 2
L A215
R B2
R A28
C(CH 3 ) 2
L A216
R B3
R A2
C(CH 3 ) 2
L A217
R B3
R A3
C(CH 3 ) 2
L A218
R B3
R A14
C(CH 3 ) 2
L A219
R B3
R A22
C(CH 3 ) 2
L A220
R B3
R A28
C(CH 3 ) 2
L A221
R B4
R A2
C(CH 3 ) 2
L A222
R B4
R A3
C(CH 3 ) 2
L A223
R B4
R A14
C(CH 3 ) 2
L A224
R B4
R A22
C(CH 3 ) 2
L A225
R B4
R A28
C(CH 3 ) 2
L A226
H
R A2
NCH 3
L A227
R A2
R A2
NCH 3
L A228
R A3
R A2
NCH 3
L A229
R A14
R A2
NCH 3
L A230
R A22
R A2
NCH 3
L A231
R A28
R A2
NCH 3
L A232
H
R A3
NCH 3
L A233
R A2
R A3
NCH 3
L A234
R A3
R A3
NCH 3
L A235
R A14
R A3
NCH 3
L A236
R A22
R A3
NCH 3
L A237
R A28
R A3
NCH 3
L A238
H
R A14
NCH 3
L A239
R A2
R A14
NCH 3
L A240
R A3
R A14
NCH 3
L A241
R A14
R A14
NCH 3
L A242
R A22
R A14
NCH 3
L A243
R A28
R A14
NCH 3
L A244
H
R A22
NCH 3
L A245
R A2
R A22
NCH 3
L A246
R A3
R A22
NCH 3
L A247
R A14
R A22
NCH 3
L A248
R A22
R A22
NCH 3
L A249
R A28
R A22
NCH 3
L A250
H
R A28
NCH 3
L A251
R A2
R A28
NCH 3
L A252
R A3
R A28
NCH 3
L A253
R A14
R A28
NCH 3
L A254
R A22
R A28
NCH 3
L A255
R A28
R A28
NCH 3
L A256
R A2
H
NCH 3
L A257
R A3
H
NCH 3
L A258
R A14
H
NCH 3
L A259
R A22
H
NCH 3
L A260
R A28
H
NCH 3
L A261
R A2
R B1
NCH 3
L A262
R A3
R B1
NCH 3
L A263
R A14
R B1
NCH 3
L A264
R A22
R B1
NCH 3
L A265
R A28
R B1
NCH 3
L A266
R A2
R B2
NCH 3
L A267
R A3
R B2
NCH 3
L A268
R A14
R B2
NCH 3
L A269
R A22
R B2
NCH 3
L A270
R A28
R B2
NCH 3
L A271
R A2
R B3
NCH 3
L A272
R A3
R B3
NCH 3
L A273
R A14
R B3
NCH 3
L A274
R A22
R B3
NCH 3
L A275
R A28
R B3
NCH 3
L A276
R A2
R B4
NCH 3
L A277
R A3
R B4
NCH 3
L A278
R A14
R B4
NCH 3
L A279
R A22
R B4
NCH 3
L A280
R A28
R B4
NCH 3
L A281
R A2
R B1
NCH 3
L A282
R A3
R B1
NCH 3
L A283
R A14
R B1
NCH 3
L A284
R A22
R B1
NCH 3
L A285
R A28
R B1
NCH 3
L A286
R A2
R B2
NCH 3
L A287
R A3
R B2
NCH 3
L A288
R A14
R B2
NCH 3
L A289
R A22
R B2
NCH 3
L A290
R A28
R B2
NCH 3
L A291
R A2
R B3
NCH 3
L A292
R A3
R B3
NCH 3
L A293
R A14
R B3
NCH 3
L A294
R A22
R B3
NCH 3
L A295
R A28
R B3
NCH 3
L A296
R A2
R B4
NCH 3
L A297
R A3
R B4
NCH 3
L A298
R A14
R B4
NCH 3
L A299
R A22
R B4
NCH 3
L A300
R A28
R B4
NCH 3
L A301
H
R A2
N(isobutyl)
L A302
R A2
R A2
N(isobutyl)
L A303
R A3
R A2
N(isobutyl)
L A304
R A14
R A2
N(isobutyl)
L A305
R A22
R A2
N(isobutyl)
L A306
R A28
R A2
N(isobutyl)
L A307
H
R A3
N(isobutyl)
L A308
R A2
R A3
N(isobutyl)
L A309
R A3
R A3
N(isobutyl)
L A310
R A14
R A3
N(isobutyl)
L A311
R A22
R A3
N(isobutyl)
L A312
R A28
R A3
N(isobutyl)
L A313
H
R A14
N(isobutyl)
L A314
R A2
R A14
N(isobutyl)
L A315
R A3
R A14
N(isobutyl)
L A316
R A14
R A14
N(isobutyl)
L A317
R A22
R A14
N(isobutyl)
L A318
R A28
R A14
N(isobutyl)
L A319
H
R A22
N(isobutyl)
L A320
R A2
R A22
N(isobutyl)
L A321
R A3
R A22
N(isobutyl)
L A322
R A14
R A22
N(isobutyl)
L A323
R A22
R A22
N(isobutyl)
L A324
R A28
R A22
N(isobutyl)
L A325
H
R A28
N(isobutyl)
L A326
R A2
R A28
N(isobutyl)
L A327
R A3
R A28
N(isobutyl)
L A328
R A14
R A28
N(isobutyl)
L A329
R A22
R A28
N(isobutyl)
L A330
R A28
R A28
N(isobutyl)
L A331
R A2
H
N(isobutyl)
L A332
R A3
H
N(isobutyl)
L A333
R A14
H
N(isobutyl)
L A334
R A22
H
N(isobutyl)
L A335
R A28
H
N(isobutyl)
L A336
R A2
R B1
N(isobutyl)
L A337
R A3
R B1
N(isobutyl)
L A338
R A14
R B1
N(isobutyl)
L A339
R A22
R B1
N(isobutyl)
L A340
R A28
R B1
N(isobutyl)
L A341
R A2
R B2
N(isobutyl)
L A342
R A3
R B2
N(isobutyl)
L A343
R A14
R B2
N(isobutyl)
L A344
R A22
R B2
N(isobutyl)
L A345
R A28
R B2
N(isobutyl)
L A346
R A2
R B3
N(isobutyl)
L A347
R A3
R B3
N(isobutyl)
L A348
R A14
R B3
N(isobutyl)
L A349
R A22
R B3
N(isobutyl)
L A350
R A28
R B3
N(isobutyl)
L A351
R A2
R B4
N(isobutyl)
L A352
R A3
R B4
N(isobutyl)
L A353
R A14
R B4
N(isobutyl)
L A354
R A22
R B4
N(isobutyl)
L A355
R A28
R B4
N(isobutyl)
L A356
R B1
R A2
N(isobutyl)
L A357
R B1
R A3
N(isobutyl)
L A358
R B1
R A14
N(isobutyl)
L A359
R B1
R A22
N(isobutyl)
L A360
R B1
R A28
N(isobutyl)
L A361
R B2
R A2
N(isobutyl)
L A362
R B2
R A3
N(isobutyl)
L A363
R B2
R A14
N(isobutyl)
L A364
R B2
R A22
N(isobutyl)
L A365
R B2
R A28
N(isobutyl)
L A366
R B3
R A2
N(isobutyl)
L A367
R B3
R A3
N(isobutyl)
L A368
R B3
R A14
N(isobutyl)
L A369
R B3
R A22
N(isobutyl)
L A370
R B3
R A28
N(isobutyl)
L A371
R B4
R A2
N(isobutyl)
L A372
R B4
R A3
N(isobutyl)
L A373
R B4
R A14
N(isobutyl)
L A374
R B4
R A22
N(isobutyl)
L A375
R B4
R A28
N(isobutyl)
and L A376 through L A750 are based on a structure of Formula V,
in which R 3 , R 4 , and X are defined as:
Ligand
R 3
R 4
X
L A376
H
R A2
O
L A377
R A2
R A2
O
L A378
R A3
R A2
O
L A379
R A14
R A2
O
L A380
R A22
R A2
O
L A381
R A28
R A2
O
L A382
H
R A3
O
L A383
R A2
R A3
O
L A384
R A3
R A3
O
L A385
R A14
R A3
O
L A386
R A22
R A3
O
L A387
R A28
R A3
O
L A388
H
R A14
O
L A389
R A2
R A14
O
L A390
R A3
R A14
O
L A391
R A14
R A14
O
L A392
R A22
R A14
O
L A393
R A28
R A14
O
L A394
H
R A22
O
L A395
R A2
R A22
O
L A396
R A3
R A22
O
L A397
R A14
R A22
O
L A398
R A22
R A22
O
L A399
R A28
R A22
O
L A400
H
R A28
O
L A401
R A2
R A28
O
L A402
R A3
R A28
O
L A403
R A14
R A28
O
L A404
R A22
R A28
O
L A405
R A28
R A28
O
L A406
R A2
H
O
L A407
R A3
H
O
L A408
R A14
H
O
L A409
R A22
H
O
L A410
R A28
H
O
L A411
R A2
R B1
O
L A412
R A3
R B1
O
L A413
R A14
R B1
O
L A414
R A22
R B1
O
L A415
R A28
R B1
O
L A416
R A2
R B2
O
L A417
R A3
R B2
O
L A418
R A14
R B2
O
L A419
R A22
R B2
O
L A420
R A28
R B2
O
L A421
R A2
R B3
O
L A422
R A3
R B3
O
L A423
R A14
R B3
O
L A424
R A22
R B3
O
L A425
R A28
R B3
O
L A426
R A2
R B4
O
L A427
R A3
R B4
O
L A428
R A14
R B4
O
L A429
R A22
R B4
O
L A430
R A28
R B4
O
L A431
R B1
R A2
O
L A432
R B1
R A3
O
L A433
R B1
R A14
O
L A434
R B1
R A22
O
L A435
R B1
R A28
O
L A436
R B2
R A2
O
L A437
R B2
R A3
O
L A438
R B2
R A14
O
L A439
R B2
R A22
O
L A440
R B2
R A28
O
L A441
R B3
R A2
O
L A442
R B3
R A3
O
L A443
R B3
R A14
O
L A444
R B3
R A22
O
L A445
R B3
R A28
O
L A446
R B4
R A2
O
L A447
R B4
R A3
O
L A448
R B4
R A14
O
L A449
R B4
R A22
O
L A450
R B4
R A28
O
L A451
H
R A2
S
L A452
R A2
R A2
S
L A453
R A3
R A2
S
L A454
R A14
R A2
S
L A455
R A22
R A2
S
L A456
R A28
R A2
S
L A457
H
R A3
S
L A458
R A2
R A3
S
L A459
R A3
R A3
S
L A460
R A14
R A3
S
L A461
R A22
R A3
S
L A462
R A28
R A3
S
L A463
H
R A14
S
L A464
R A2
R A14
S
L A465
R A3
R A14
S
L A466
R A14
R A14
S
L A467
R A22
R A14
S
L A468
R A28
R A14
S
L A469
H
R A22
S
L A470
R A2
R A22
S
L A471
R A3
R A22
S
L A472
R A14
R A22
S
L A473
R A22
R A22
S
L A474
R A28
R A22
S
L A475
H
R A28
S
L A476
R A2
R A28
S
L A477
R A3
R A28
S
L A478
R A14
R A28
S
L A479
R A22
R A28
S
L A480
R A28
R A28
S
L A481
R A2
H
S
L A482
R A3
H
S
L A483
R A14
H
S
L A484
R A22
H
S
L A485
R A28
H
S
L A486
R A2
R B1
S
L A487
R A3
R B1
S
L A488
R A14
R B1
S
L A489
R A22
R B1
S
L A490
R A28
R B1
S
L A491
R A2
R B2
S
L A492
R A3
R B2
S
L A493
R A14
R B2
S
L A494
R A22
R B2
S
L A495
R A28
R B2
S
L A496
R A2
R B3
S
L A497
R A3
R B3
S
L A498
R A14
R B3
S
L A499
R A22
R B3
S
L A500
R A28
R B3
S
L A501
R A2
R B4
S
L A502
R A3
R B4
S
L A503
R A14
R B4
S
L A504
R A22
R B4
S
L A505
R A28
R B4
S
L A506
R B1
R A2
S
L A507
R B1
R A3
S
L A508
R B1
R A14
S
L A509
R B1
R A22
S
L A510
R B1
R A28
S
L A511
R B2
R A2
S
L A512
R B2
R A3
S
L A513
R B2
R A14
S
L A514
R B2
R A22
S
L A515
R B2
R A28
S
L A516
R B3
R A2
S
L A517
R B3
R A3
S
L A518
R B3
R A14
S
L A519
R B3
R A22
S
L A520
R B3
R A28
S
L A521
R B4
R A2
S
L A522
R B4
R A3
S
L A523
R B4
R A14
S
L A524
R B4
R A22
S
L A525
R B4
R A28
S
L A526
H
R A2
C(CH 3 ) 2
L A527
R A2
R A2
C(CH 3 ) 2
L A528
R A3
R A2
C(CH 3 ) 2
L A529
R A14
R A2
C(CH 3 ) 2
L A530
R A22
R A2
C(CH 3 ) 2
L A531
R A28
R A2
C(CH 3 ) 2
L A532
H
R A3
C(CH 3 ) 2
L A533
R A2
R A3
C(CH 3 ) 2
L A534
R A3
R A3
C(CH 3 ) 2
L A535
R A14
R A3
C(CH 3 ) 2
L A536
R A22
R A3
C(CH 3 ) 2
L A537
R A28
R A3
C(CH 3 ) 2
L A538
H
R A14
C(CH 3 ) 2
L A539
R A2
R A14
C(CH 3 ) 2
L A540
R A3
R A14
C(CH 3 ) 2
L A541
R A14
R A14
C(CH 3 ) 2
L A542
R A22
R A14
C(CH 3 ) 2
L A543
R A28
R A14
C(CH 3 ) 2
L A544
H
R A22
C(CH 3 ) 2
L A545
R A2
R A22
C(CH 3 ) 2
L A546
R A3
R A22
C(CH 3 ) 2
L A547
R A14
R A22
C(CH 3 ) 2
L A548
R A22
R A22
C(CH 3 ) 2
L A549
R A28
R A22
C(CH 3 ) 2
L A550
H
R A28
C(CH 3 ) 2
L A551
R A2
R A28
C(CH 3 ) 2
L A552
R A3
R A28
C(CH 3 ) 2
L A553
R A14
R A28
C(CH 3 ) 2
L A554
R A22
R A28
C(CH 3 ) 2
L A555
R A28
R A28
C(CH 3 ) 2
L A556
R A2
H
C(CH 3 ) 2
L A557
R A3
H
C(CH 3 ) 2
L A558
R A14
H
C(CH 3 ) 2
L A559
R A22
H
C(CH 3 ) 2
L A560
R A28
H
C(CH 3 ) 2
L A561
R A2
R B1
C(CH 3 ) 2
L A562
R A3
R B1
C(CH 3 ) 2
L A563
R A14
R B1
C(CH 3 ) 2
L A564
R A22
R B1
C(CH 3 ) 2
L A565
R A28
R B1
C(CH 3 ) 2
L A566
R A2
R B2
C(CH 3 ) 2
L A567
R A3
R B2
C(CH 3 ) 2
L A568
R A14
R B2
C(CH 3 ) 2
L A569
R A22
R B2
C(CH 3 ) 2
L A570
R A28
R B2
C(CH 3 ) 2
L A571
R A2
R B3
C(CH 3 ) 2
L A572
R A3
R B3
C(CH 3 ) 2
L A573
R A14
R B3
C(CH 3 ) 2
L A574
R A22
R B3
C(CH 3 ) 2
L A575
R A28
R B3
C(CH 3 ) 2
L A576
R A2
R B4
C(CH 3 ) 2
L A577
R A3
R B4
C(CH 3 ) 2
L A578
R A14
R B4
C(CH 3 ) 2
L A579
R A22
R B4
C(CH 3 ) 2
L A580
R A28
R B4
C(CH 3 ) 2
L A581
R B1
R A2
C(CH 3 ) 2
L A582
R B1
R A3
C(CH 3 ) 2
L A583
R B1
R A14
C(CH 3 ) 2
L A584
R B1
R A22
C(CH 3 ) 2
L A585
R B1
R A28
C(CH 3 ) 2
L A586
R B2
R A2
C(CH 3 ) 2
L A587
R B2
R A3
C(CH 3 ) 2
L A588
R B2
R A14
C(CH 3 ) 2
L A589
R B2
R A22
C(CH 3 ) 2
L A590
R B2
R A28
C(CH 3 ) 2
L A591
R B3
R A2
C(CH 3 ) 2
L A592
R B3
R A3
C(CH 3 ) 2
L A593
R B3
R A14
C(CH 3 ) 2
L A594
R B3
R A22
C(CH 3 ) 2
L A595
R B3
R A28
C(CH 3 ) 2
L A596
R B4
R A2
C(CH 3 ) 2
L A597
R B4
R A3
C(CH 3 ) 2
L A598
R B4
R A14
C(CH 3 ) 2
L A599
R B4
R A22
C(CH 3 ) 2
L A600
R B4
R A28
C(CH 3 ) 2
L A601
H
R A2
NCH 3
L A602
R A2
R A2
NCH 3
L A603
R A3
R A2
NCH 3
L A604
R A14
R A2
NCH 3
L A605
R A22
R A2
NCH 3
L A606
R A28
R A2
NCH 3
L A607
H
R A3
NCH 3
L A608
R A2
R A3
NCH 3
L A609
R A3
R A3
NCH 3
L A610
R A14
R A3
NCH 3
L A611
R A22
R A3
NCH 3
L A612
R A28
R A3
NCH 3
L A613
H
R A14
NCH 3
L A614
R A2
R A14
NCH 3
L A615
R A3
R A14
NCH 3
L A616
R A14
R A14
NCH 3
L A617
R A22
R A14
NCH 3
L A618
R A28
R A14
NCH 3
L A619
H
R A22
NCH 3
L A620
R A2
R A22
NCH 3
L A621
R A3
R A22
NCH 3
L A622
R A14
R A22
NCH 3
L A623
R A22
R A22
NCH 3
L A624
R A28
R A22
NCH 3
L A625
H
R A28
NCH 3
L A626
R A2
R A28
NCH 3
L A627
R A3
R A28
NCH 3
L A628
R A14
R A28
NCH 3
L A629
R A22
R A28
NCH 3
L A630
R A28
R A28
NCH 3
L A631
R A2
H
NCH 3
L A632
R A3
H
NCH 3
L A633
R A14
H
NCH 3
L A634
R A22
H
NCH 3
L A635
R A28
H
NCH 3
L A636
R A2
R B1
NCH 3
L A637
R A3
R B1
NCH 3
L A638
R A14
R B1
NCH 3
L A639
R A22
R B1
NCH 3
L A640
R A28
R B1
NCH 3
L A641
R A2
R B2
NCH 3
L A642
R A3
R B2
NCH 3
L A643
R A14
R B2
NCH 3
L A644
R A22
R B2
NCH 3
L A645
R A28
R B2
NCH 3
L A646
R A2
R B3
NCH 3
L A647
R A3
R B3
NCH 3
L A648
R A14
R B3
NCH 3
L A649
R A22
R B3
NCH 3
L A650
R A28
R B3
NCH 3
L A651
R A2
R B4
NCH 3
L A652
R A3
R B4
NCH 3
L A653
R A14
R B4
NCH 3
L A654
R A22
R B4
NCH 3
L A655
R A28
R B4
NCH 3
L A656
R A2
R B1
NCH 3
L A657
R A3
R B1
NCH 3
L A658
R A14
R B1
NCH 3
L A659
R A22
R B1
NCH 3
L A660
R A28
R B1
NCH 3
L A661
R A2
R B2
NCH 3
L A662
R A3
R B2
NCH 3
L A663
R A14
R B2
NCH 3
L A664
R A22
R B2
NCH 3
L A665
R A28
R B2
NCH 3
L A666
R A2
R B3
NCH 3
L A667
R A3
R B3
NCH 3
L A668
R A14
R B3
NCH 3
L A669
R A22
R B3
NCH 3
L A670
R A28
R B3
NCH 3
L A671
R A2
R B4
NCH 3
L A672
R A3
R B4
NCH 3
L A673
R A14
R B4
NCH 3
L A674
R A22
R B4
NCH 3
L A675
R A28
R B4
NCH 3
L A676
H
R A2
N(isobutyl)
L A677
R A2
R A2
N(isobutyl)
L A678
R A3
R A2
N(isobutyl)
L A679
R A14
R A2
N(isobutyl)
L A680
R A22
R A2
N(isobutyl)
L A681
R A28
R A2
N(isobutyl)
L A682
H
R A3
N(isobutyl)
L A683
R A2
R A3
N(isobutyl)
L A684
R A3
R A3
N(isobutyl)
L A685
R A14
R A3
N(isobutyl)
L A686
R A22
R A3
N(isobutyl)
L A687
R A28
R A3
N(isobutyl)
L A688
H
R A14
N(isobutyl)
L A689
R A2
R A14
N(isobutyl)
L A690
R A3
R A14
N(isobutyl)
L A691
R A14
R A14
N(isobutyl)
L A692
R A22
R A14
N(isobutyl)
L A693
R A28
R A14
N(isobutyl)
L A694
H
R A22
N(isobutyl)
L A695
R A2
R A22
N(isobutyl)
L A696
R A3
R A22
N(isobutyl)
L A697
R A14
R A22
N(isobutyl)
L A698
R A22
R A22
N(isobutyl)
L A699
R A28
R A22
N(isobutyl)
L A700
H
R A28
N(isobutyl)
L A701
R A2
R A28
N(isobutyl)
L A702
R A3
R A28
N(isobutyl)
L A703
R A14
R A28
N(isobutyl)
L A704
R A22
R A28
N(isobutyl)
L A705
R A28
R A28
N(isobutyl)
L A706
R A2
H
N(isobutyl)
L A707
R A3
H
N(isobutyl)
L A708
R A14
H
N(isobutyl)
L A709
R A22
H
N(isobutyl)
L A710
R A28
H
N(isobutyl)
L A711
R A2
R B1
N(isobutyl)
L A712
R A3
R B1
N(isobutyl)
L A713
R A14
R B1
N(isobutyl)
L A714
R A22
R B1
N(isobutyl)
L A715
R A28
R B1
N(isobutyl)
L A716
R A2
R B2
N(isobutyl)
L A717
R A3
R B2
N(isobutyl)
L A718
R A14
R B2
N(isobutyl)
L A719
R A22
R B2
N(isobutyl)
L A720
R A28
R B2
N(isobutyl)
L A721
R A2
R B3
N(isobutyl)
L A722
R A3
R B3
N(isobutyl)
L A723
R A14
R B3
N(isobutyl)
L A724
R A22
R B3
N(isobutyl)
L A725
R A28
R B3
N(isobutyl)
L A726
R A2
R B4
N(isobutyl)
L A727
R A3
R B4
N(isobutyl)
L A728
R A14
R B4
N(isobutyl)
L A729
R A22
R B4
N(isobutyl)
L A730
R A28
R B4
N(isobutyl)
L A731
R B1
R A2
N(isobutyl)
L A732
R B1
R A3
N(isobutyl)
L A733
R B1
R A14
N(isobutyl)
L A734
R B1
R A22
N(isobutyl)
L A735
R B1
R A28
N(isobutyl)
L A736
R B2
R A2
N(isobutyl)
L A737
R B2
R A3
N(isobutyl)
L A738
R B2
R A14
N(isobutyl)
L A739
R B2
R A22
N(isobutyl)
L A740
R B2
R A28
N(isobutyl)
L A741
R B3
R A2
N(isobutyl)
L A742
R B3
R A3
N(isobutyl)
L A743
R B3
R A14
N(isobutyl)
L A744
R B3
R A22
N(isobutyl)
L A745
R B3
R A28
N(isobutyl)
L A746
R B4
R A2
N(isobutyl)
L A747
R B4
R A3
N(isobutyl)
L A748
R B4
R A14
N(isobutyl)
L A749
R B4
R A22
N(isobutyl)
L A750
R B4
R A28
N(isobutyl)
wherein R B1 to R B4 have the following structures:
12. The compound of claim 1 , wherein the compound has a structure of Formula III, (L A ) n Ir(L B ) 3-n , wherein L B is a bidentate ligand and n is 1, 2, or 3.
13. The compound of claim 12 , wherein the ligand L B is selected from the group consisting of:
14. The compound of claim 11 , wherein the compound is selected from the group consisting of Compound 1 through Compound 12,750;
wherein each Compound x has the formula Ir(L Ak ) 2 (L Bj );
wherein x=750j+k−750, k is an integer from 1 to 750, and j is an integer from 1 to 17; and
wherein ligands L B1 through L B17 are defined as follows:
15. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L A of Formula I:
wherein ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R is fused to ring B and has a structure of Formula II:
wherein the wave lines indicate bonds to ring B;
wherein R 1 represents mono, di, tri, or tetra substitution, or no substitution;
wherein R 2 represents mono or di substitution, or no substitution;
wherein X 1 , X 2 , X 3 , and X 4 are each independently carbon or nitrogen;
wherein at least one of X 1 to X 4 is nitrogen;
wherein at least two adjacent of X 1 , X 2 , X 3 , and X 4 are carbon and fuse to R;
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 1 , R 2 , R 3 , R 4 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any two adjacent substituents are optionally joined to form into a ring;
wherein at least one of R 3 and R 4 comprises a chemical group selected from the group consisting of alkyl, cycloalkyl, partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;
wherein L A is coordinated to a metal M;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.
16. The first device of claim 15 , wherein the first 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 first 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 first device 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 carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
19. The first 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.
20. A formulation comprising a compound comprising a ligand L A of Formula I:
wherein ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R is fused to ring B and has a structure of Formula II:
wherein the wave lines indicate bonds to ring B;
wherein R 1 represents mono, di, tri, or tetra substitution, or no substitution;
wherein R 2 represents mono or di substitution, or no substitution;
wherein X 1 , X 2 , X 3 , and X 4 are each independently carbon or nitrogen;
wherein at least one of X 1 to X 4 is nitrogen;
wherein at least two adjacent of X 1 , X 2 , X 3 , and X 4 are carbon and fuse to R;
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 1 , R 2 , R 3 , R 4 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any two adjacent substituents are optionally joined to form into a ring;
wherein at least one of R 3 and R 4 comprises a chemical group selected from the group consisting of alkyl, cycloalkyl, partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;
wherein the ligand L A is coordinated to a metal M;
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.Cited by (0)
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