Organic electroluminescent materials and devices
Provided are novel Iridium and Platinum complexes containing heterocyclic benzo-fused ligands. The disclosed compound can include a ligand L A having a structure of Formula I: Also provided are formulations comprising these novel Iridium and Platinum complexes. Further provided are OLEDs and related consumer products that utilize these novel Iridium and Platinum complexes.
1 . A compound comprising a ligand L A having a structure of Formula I:
wherein:
ring A is a 6-membered aromatic ring;
ring D is a monocyclic or multicyclic fused ring system comprising one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
K is selected from the group consisting of a direct bond, 0, and S;
R A represents zero, mono, or up to a maximum allowable substitution to its associated ring;
R D represents di or up to a maximum allowable substitution to its associated ring;
at least two adjacent R D form a structure of Formula II fused to D;
Z 1 is selected from the group consisting of O, S, Se, NR, and SiRR′;
Z 2 is N;
if ring D is benzene, then neither Z 1 nor Z 2 are fused to D at the carbon ring atom adjacent to the carbon ring atom that bonds to K;
each R A , R B , R D , R, and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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;
the ligand L A complexes to a metal M through the dashed lines to form a 5-membered chelate ring;
M is Ir;
M can be coordinated to other ligands;
L A can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
any two of R A , R B , R D , R, and R′ can be joined or fused to form a ring;
at least one of the following is true:
(1) ring D is a multicyclic fused ring system wherein the ring of said multicyclic fused ring system that is directly coordinated to M is a 6-membered carbocyclic ring, and wherein Formula II is directly fused to a 6-membered ring of said multicyclic fused ring structure that is not directly coordinated to M,
(2) ring D is benzene, and Z 1 or Z 2 is bonded to an atom ortho to the bond with ring A,
(3) ring D is benzene, and Z 1 or Z 2 is bonded para to the bond with metal M,
(4) at least one R A or R B comprises a moiety selected from at least two rings that are not fused together, partially or fully deuterated alkyl, or partially or fully deuterated cycloalkyl, or
(5) K is O or S; and
if condition (1), condition (2), condition (3), or condition (4) is true, then the compound has a formula selected from the group consisting of Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), and Ir(L A )(L B )(L C ), wherein L C is a bidentate ligand, wherein L A , L B , and L C are different from each other, and wherein L B is selected from the group consisting of
wherein:
T is B, Al, Ga, or In;
each of Y 1 to Y 13 is independently selected from the group consisting of C and N;
Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
each R a , R b , R c , and R d independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e , and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; the general substituents defined herein; and
any two adjacent R a , R b , R c , R d , R e , and R f can be fused or joined to form a ring or form a multidentate ligand.
2 . The compound of claim 1 , wherein each R A , R B , R D , R, and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, boryl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
3 . The compound of claim 1 , wherein ring D is benzene, and Z 1 or Z 2 is bonded para to the bond with metal M.
4 . The compound of claim 1 , wherein R B is selected from the group consisting of
5 . The compound of claim 1 , wherein ring D is selected from the group consisting of benzene, naphthalene, anthracene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, and aza-variants thereof; and ring A is selected from the group consisting of pyridine, pyrimidine, pyridazine, quinoline, isoquinoline, quinoxaline, quinazoline, thienopyridine, thienopyrimidine, thienopyridazine, azadibenzofuran, azadibenzothiophene, azabenzofuran, and azabenzothiophene.
6 . The compound of claim 1 , wherein the structure of Formula II is selected from the group consisting of:
7 . The compound of claim 1 , wherein L A is selected from the group consisting
wherein Z 1′ =O, S, or NCH 3 ; Z 2′ , Z 3′ , Z 4′ =C, or N; and Z 5 =O, N, S, Si(CH 3 ) 2 , or C(CH 3 ) 2 .
8 . The compound of claim 1 , wherein L A is selected from the group consisting of L Ai-m wherein i is an integer from 1 to 2100 and m is an integer from 1 to 4, 6 to 8, 10 to 13, 15 to 37, 40, 41, and 44 to 66, wherein the structures of L Ai-1 to L Ai-4 , L Ai-6 to L Ai-8 , L Ai-10 to L Ai-13 , L Ai-15 to L Ai-37 , L Ai-40 , L Ai-41 , and L Ai-44 to L Ai-66 are as shown below:
wherein R A and R B for each L A , are defined below:
Ligand
R A
R B
L A1
R A1
R B1
L A2
R A2
R B1
L A3
R A3
R B1
L A4
R A4
R B1
L A5
R A5
R B1
L A6
R A6
R B1
L A7
R A7
R B1
L A8
R A8
R B1
L A9
R A9
R B1
L A10
R A10
R B1
L A11
R A11
R B1
L A12
R A12
R B1
L A13
R A13
R B1
L A14
R A14
R B1
L A15
R A15
R B1
L A16
R A16
R B1
L A17
R A17
R B1
L A18
R A18
R B1
L A19
R A19
R B1
L A20
R A20
R B1
L A21
R A21
R B1
L A22
R A22
R B1
L A23
R A23
R B1
L A24
R A24
R B1
L A25
R A25
R B1
L A26
R A26
R B1
L A27
R A27
R B1
L A28
R A28
R B1
L A29
R A29
R B1
L A30
R A30
R B1
L A31
R A31
R B1
L A32
R A32
R B1
L A33
R A33
R B1
L A34
R A34
R B1
L A35
R A35
R B1
L A36
R A36
R B1
L A37
R A37
R B1
L A38
R A38
R B1
L A39
R A39
R B1
L A40
R A40
R B1
L A41
R A41
R B1
L A42
R A42
R B1
L A43
R A43
R B1
L A44
R A44
R B1
L A45
R A45
R B1
L A46
R A46
R B1
L A47
R A47
R B1
L A48
R A48
R B1
L A49
R A49
R B1
L A50
R A50
R B1
L A51
R A51
R B1
L A52
R A52
R B1
L A53
R A53
R B1
L A54
R A54
R B1
L A55
R A55
R B1
L A56
R A56
R B1
L A57
R A57
R B1
L A58
R A58
R B1
L A59
R A59
R B1
L A60
R A60
R B1
L A61
R A61
R B1
L A62
R A62
R B1
L A63
R A63
R B1
L A64
R A64
R B1
L A65
R A65
R B1
L A66
R A66
R B1
L A67
R A67
R B1
L A68
R A68
R B1
L A69
R A69
R B1
L A70
R A70
R B1
L A71
R A1
R B2
L A72
R A2
R B2
L A73
R A3
R B2
L A74
R A4
R B2
L A75
R A5
R B2
L A76
R A6
R B2
L A77
R A7
R B2
L A78
R A8
R B2
L A79
R A9
R B2
L A80
R A10
R B2
L A81
R A11
R B2
L A82
R A12
R B2
L A83
R A13
R B2
L A84
R A14
R B2
L A85
R A15
R B2
L A86
R A16
R B2
L A87
R A17
R B2
L A88
R A18
R B2
L A89
R A19
R B2
L A90
R A20
R B2
L A91
R A21
R B2
L A92
R A22
R B2
L A93
R A23
R B2
L A94
R A24
R B2
L A95
R A25
R B2
L A96
R A26
R B2
L A97
R A27
R B2
L A98
R A28
R B2
L A99
R A29
R B2
L A100
R A30
R B2
L A101
R A31
R B2
L A102
R A32
R B2
L A103
R A33
R B2
L A104
R A34
R B2
L A105
R A35
R B2
L A106
R A36
R B2
L A107
R A37
R B2
L A108
R A38
R B2
L A109
R A39
R B2
L A110
R A40
R B2
L A111
R A41
R B2
L A112
R A42
R B2
L A113
R A43
R B2
L A114
R A44
R B2
L A115
R A45
R B2
L A116
R A46
R B2
L A117
R A47
R B2
L A118
R A48
R B2
L A119
R A49
R B2
L A120
R A50
R B2
L A121
R A51
R B2
L A122
R A52
R B2
L A123
R A53
R B2
L A124
R A54
R B2
L A125
R A55
R B2
L A126
R A56
R B2
L A127
R A57
R B2
L A128
R A58
R B2
L A129
R A59
R B2
L A130
R A60
R B2
L A131
R A61
R B2
L A132
R A62
R B2
L A133
R A63
R B2
L A134
R A64
R B2
L A135
R A65
R B2
L A136
R A66
R B2
L A137
R A67
R B2
L A138
R A68
R B2
L A139
R A69
R B2
L A140
R A70
R B2
L A141
R A1
R B3
L A142
R A2
R B3
L A143
R A3
R B3
L A144
R A4
R B3
L A145
R A5
R B3
L A146
R A6
R B3
L A147
R A7
R B3
L A148
R A8
R B3
L A149
R A9
R B3
L A150
R A10
R B3
L A151
R A11
R B3
L A152
R A12
R B3
L A153
R A13
R B3
L A154
R A14
R B3
L A155
R A15
R B3
L A156
R A16
R B3
L A157
R A17
R B3
L A158
R A18
R B3
L A159
R A19
R B3
L A160
R A20
R B3
L A161
R A21
R B3
L A162
R A22
R B3
L A163
R A23
R B3
L A164
R A24
R B3
L A165
R A25
R B3
L A166
R A26
R B3
L A167
R A27
R B3
L A168
R A28
R B3
L A169
R A29
R B3
L A170
R A30
R B3
L A171
R A31
R B3
L A172
R A32
R B3
L A173
R A33
R B3
L A174
R A34
R B3
L A175
R A35
R B3
L A176
R A36
R B3
L A177
R A37
R B3
L A178
R A38
R B3
L A179
R A39
R B3
L A180
R A40
R B3
L A181
R A41
R B3
L A182
R A42
R B3
L A183
R A43
R B3
L A184
R A44
R B3
L A185
R A45
R B3
L A186
R A46
R B3
L A187
R A47
R B3
L A188
R A48
R B3
L A189
R A49
R B3
L A190
R A50
R B3
L A191
R A51
R B3
L A192
R A52
R B3
L A193
R A53
R B3
L A194
R A54
R B3
L A195
R A55
R B3
L A196
R A56
R B3
L A197
R A57
R B3
L A198
R A58
R B3
L A199
R A59
R B3
L A200
R A60
R B3
L A201
R A61
R B3
L A202
R A62
R B3
L A203
R A63
R B3
L A204
R A64
R B3
L A205
R A65
R B3
L A206
R A66
R B3
L A207
R A67
R B3
L A208
R A68
R B3
L A209
R A69
R B3
L A210
R A70
R B3
L A211
R A1
R B4
L A212
R A2
R B4
L A213
R A3
R B4
L A214
R A4
R B4
L A215
R A5
R B4
L A216
R A6
R B4
L A217
R A7
R B4
L A218
R A8
R B4
L A219
R A9
R B4
L A220
R A10
R B4
L A221
R A11
R B4
L A222
R A12
R B4
L A223
R A13
R B4
L A224
R A14
R B4
L A225
R A15
R B4
L A226
R A16
R B4
L A227
R A17
R B4
L A228
R A18
R B4
L A229
R A19
R B4
L A230
R A20
R B4
L A231
R A21
R B4
L A232
R A22
R B4
L A233
R A23
R B4
L A234
R A24
R B4
L A235
R A25
R B4
L A236
R A26
R B4
L A237
R A27
R B4
L A238
R A28
R B4
L A239
R A29
R B4
L A240
R A30
R B4
L A241
R A31
R B4
L A242
R A32
R B4
L A243
R A33
R B4
L A244
R A34
R B4
L A245
R A35
R B4
L A246
R A36
R B4
L A247
R A37
R B4
L A248
R A38
R B4
L A249
R A39
R B4
L A250
R A40
R B4
L A251
R A41
R B4
L A252
R A42
R B4
L A253
R A43
R B4
L A254
R A44
R B4
L A255
R A45
R B4
L A256
R A46
R B4
L A257
R A47
R B4
L A258
R A48
R B4
L A259
R A49
R B4
L A260
R A50
R B4
L A261
R A51
R B4
L A262
R A52
R B4
L A263
R A53
R B4
L A264
R A54
R B4
L A265
R A55
R B4
L A266
R A56
R B4
L A267
R A57
R B4
L A268
R A58
R B4
L A269
R A59
R B4
L A270
R A60
R B4
L A271
R A61
R B4
L A272
R A62
R B4
L A273
R A63
R B4
L A274
R A64
R B4
L A275
R A65
R B4
L A276
R A66
R B4
L A277
R A67
R B4
L A278
R A68
R B4
L A279
R A69
R B4
L A280
R A70
R B4
L A281
R A1
R B5
L A282
R A2
R B5
L A283
R A3
R B5
L A284
R A4
R B5
L A285
R A5
R B5
L A286
R A6
R B5
L A287
R A7
R B5
L A288
R A8
R B5
L A289
R A9
R B5
L A290
R A10
R B5
L A291
R A11
R B5
L A292
R A12
R B5
L A293
R A13
R B5
L A294
R A14
R B5
L A295
R A15
R B5
L A296
R A16
R B5
L A297
R A17
R B5
L A298
R A18
R B5
L A299
R A19
R B5
L A300
R A20
R B5
L A301
R A21
R B5
L A302
R A22
R B5
L A303
R A23
R B5
L A304
R A24
R B5
L A305
R A25
R B5
L A306
R A26
R B5
L A307
R A27
R B5
L A308
R A28
R B5
L A309
R A29
R B5
L A310
R A30
R B5
L A311
R A31
R B5
L A312
R A32
R B5
L A313
R A33
R B5
L A314
R A34
R B5
L A315
R A35
R B5
L A316
R A36
R B5
L A317
R A37
R B5
L A318
R A38
R B5
L A319
R A39
R B5
L A320
R A40
R B5
L A321
R A41
R B5
L A322
R A42
R B5
L A323
R A43
R B5
L A324
R A44
R B5
L A325
R A45
R B5
L A326
R A46
R B5
L A327
R A47
R B5
L A328
R A48
R B5
L A329
R A49
R B5
L A330
R A50
R B5
L A331
R A51
R B5
L A332
R A52
R B5
L A333
R A53
R B5
L A334
R A54
R B5
L A335
R A55
R B5
L A336
R A56
R B5
L A337
R A57
R B5
L A338
R A58
R B5
L A339
R A59
R B5
L A340
R A60
R B5
L A341
R A61
R B5
L A342
R A62
R B5
L A343
R A63
R B5
L A344
R A64
R B5
L A345
R A65
R B5
L A346
R A66
R B5
L A347
R A67
R B5
L A348
R A68
R B5
L A349
R A69
R B5
L A350
R A70
R B5
L A351
R A1
R B6
L A352
R A2
R B6
L A353
R A3
R B6
L A354
R A4
R B6
L A355
R A5
R B6
L A356
R A6
R B6
L A357
R A7
R B6
L A358
R A8
R B6
L A359
R A9
R B6
L A360
R A10
R B6
L A361
R A11
R B6
L A362
R A12
R B6
L A363
R A13
R B6
L A364
R A14
R B6
L A365
R A15
R B6
L A366
R A16
R B6
L A367
R A17
R B6
L A368
R A18
R B6
L A369
R A19
R B6
L A370
R A20
R B6
L A371
R A21
R B6
L A372
R A22
R B6
L A373
R A23
R B6
L A374
R A24
R B6
L A375
R A25
R B6
L A376
R A26
R B6
L A377
R A27
R B6
L A378
R A28
R B6
L A379
R A29
R B6
L A380
R A30
R B6
L A381
R A31
R B6
L A382
R A32
R B6
L A383
R A33
R B6
L A384
R A34
R B6
L A385
R A35
R B6
L A386
R A36
R B6
L A387
R A37
R B6
L A388
R A38
R B6
L A389
R A39
R B6
L A390
R A40
R B6
L A391
R A41
R B6
L A392
R A42
R B6
L A393
R A43
R B6
L A394
R A44
R B6
L A395
R A45
R B6
L A396
R A46
R B6
L A397
R A47
R B6
L A398
R A48
R B6
L A399
R A49
R B6
L A400
R A50
R B6
L A401
R A51
R B6
L A402
R A52
R B6
L A403
R A53
R B6
L A404
R A54
R B6
L A405
R A55
R B6
L A406
R A56
R B6
L A407
R A57
R B6
L A408
R A58
R B6
L A409
R A59
R B6
L A410
R A60
R B6
L A411
R A61
R B6
L A412
R A62
R B6
L A413
R A63
R B6
L A414
R A64
R B6
L A415
R A65
R B6
L A416
R A66
R B6
L A417
R A67
R B6
L A418
R A68
R B6
L A419
R A69
R B6
L A420
R A70
R B6
L A421
R A1
R B7
L A422
R A2
R B7
L A423
R A3
R B7
L A424
R A4
R B7
L A425
R A5
R B7
L A426
R A6
R B7
L A427
R A7
R B7
L A428
R A8
R B7
L A429
R A9
R B7
L A430
R A10
R B7
L A431
R A11
R B7
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R A70
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L A1962
R A2
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R A6
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R A12
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R A17
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R B29
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R B29
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R A31
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R A32
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L A1999
R A39
R B29
L A2000
R A40
R B29
L A2001
R A41
R B29
L A2002
R A42
R B29
L A2003
R A43
R B29
L A2004
R A44
R B29
L A2005
R A45
R B29
L A2006
R A46
R B29
L A2007
R A47
R B29
L A2008
R A48
R B29
L A2009
R A49
R B29
L A2010
R A50
R B29
L A2011
R A51
R B29
L A2012
R A52
R B29
L A2013
R A53
R B29
L A2014
R A54
R B29
L A2015
R A55
R B29
L A2016
R A56
R B29
L A2017
R A57
R B29
L A2018
R A58
R B29
L A2019
R A59
R B29
L A2020
R A60
R B29
L A2021
R A61
R B29
L A2022
R A62
R B29
L A2023
R A63
R B29
L A2024
R A64
R B29
L A2025
R A65
R B29
L A2026
R A66
R B29
L A2027
R A67
R B29
L A2028
R A68
R B29
L A2029
R A69
R B29
L A2030
R A70
R B29
L A2031
R A1
R B30
L A2032
R A2
R B30
L A2033
R A3
R B30
L A2034
R A4
R B30
L A2035
R A5
R B30
L A2036
R A6
R B30
L A2037
R A7
R B30
L A2038
R A8
R B30
L A2039
R A9
R B30
L A2040
R A10
R B30
L A2041
R A11
R B30
L A2042
R A12
R B30
L A2043
R A13
R B30
L A2044
R A14
R B30
L A2045
R A15
R B30
L A2046
R A16
R B30
L A2047
R A17
R B30
L A2048
R A18
R B30
L A2049
R A19
R B30
L A2050
R A20
R B30
L A2051
R A21
R B30
L A2052
R A22
R B30
L A2053
R A23
R B30
L A2054
R A24
R B30
L A2055
R A25
R B30
L A2056
R A26
R B30
L A2057
R A27
R B30
L A2058
R A28
R B30
L A2059
R A29
R B30
L A2060
R A30
R B30
L A2061
R A31
R B30
L A2062
R A32
R B30
L A2063
R A33
R B30
L A2064
R A34
R B30
L A2065
R A35
R B30
L A2066
R A36
R B30
L A2067
R A37
R B30
L A2068
R A38
R B30
L A2069
R A39
R B30
L A2070
R A40
R B30
L A2071
R A41
R B30
L A2072
R A42
R B30
L A2073
R A43
R B30
L A2074
R A44
R B30
L A2075
R A45
R B30
L A2076
R A46
R B30
L A2077
R A47
R B30
L A2078
R A48
R B30
L A2079
R A49
R B30
L A2080
R A50
R B30
L A2081
R A51
R B30
L A2082
R A52
R B30
L A2083
R A53
R B30
L A2084
R A54
R B30
L A2085
R A55
R B30
L A2086
R A56
R B30
L A2087
R A57
R B30
L A2088
R A58
R B30
L A2089
R A59
R B30
L A2090
R A60
R B30
L A2091
R A61
R B30
L A2092
R A62
R B30
L A2093
R A63
R B30
L A2094
R A64
R B30
L A2095
R A65
R B30
L A2096
R A66
R B30
L A2097
R A67
R B30
L A2098
R A68
R B30
L A2099
R A69
R B30
L A2100
R A70
R B30
with the proviso that if L A has a structure of L Ai-15 or L Ai-16 , then at least one of the following must be true: (i) R A is R A5 , R A8 , R A9 , R A11 , R A14 , R A15 , R A20 -R A22 , R A25 -R A57 , R A59 -R A66 , R A68 , or R A70 , or (ii) R B is R B3 , R B6 , R B9 , R B11 -R B14 , R B16 , R B18 -R B20 , R B22 , R B28 , R B29 , or R B30 ;
wherein R A to R A7 have the following structures:
wherein R B1 to R B30 have the following structures:
9 . The compound of claim 1 , wherein the compound has a formula selected from the group consisting of Ir(L A ) 3 , Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), Ir(L A ) 2 (L C ), and Ir(L A )(L B )(L C ); and wherein L A , L B , and L C are different from each other; and L B and L C are each independently selected from the group consisting of:
wherein:
T is B, Al, Ga, or In;
each of Y 1 to Y 13 is independently selected from the group consisting of C and N;
Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
R e and R f can be fused or joined to form a ring;
each R a , R b , R c , and R d independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, the general substituents defined herein; and
any two adjacent R a , R b , R c , R d , R e and R f can be fused or joined to form a ring or form a multidentate ligand.
10 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
11 . 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 comprising a ligand L A having a structure of:
wherein:
ring A is a 6-membered aromatic ring;
ring D is a monocyclic or multicyclic fused ring system comprising one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
K is selected from the group consisting of a direct bond, 0, and S;
R A represents zero, mono, or up to a maximum allowable substitution to its associated ring;
R D represents di or up to a maximum allowable substitution to its associated ring;
at least two adjacent R D form a structure of Formula II fused to D;
Z 1 is selected from the group consisting of O, S, Se, NR, and SiRR′;
Z 2 is N;
if ring D is benzene, then neither Z 1 nor Z 2 are fused to D at the carbon ring atom adjacent to the carbon ring atom that bonds to K;
each R A , R B , R D , R, and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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;
the ligand L A complexes to a metal M through the dashed lines to form a 5-membered chelate ring;
M is Ir;
M can be coordinated to other ligands;
L A can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
any two of R A , R B , R D , R, and R′ can be joined or fused to form a ring;
at least one of the following is true:
(1) ring D is a multicyclic fused ring system wherein the ring of said multicyclic fused ring system that is directly coordinated to M is a 6-membered carbocyclic ring, and wherein Formula II is directly fused to a 6-membered ring of said multicyclic fused ring structure that is not directly coordinated to M,
(2) ring D is benzene, and a Z 1 or Z 2 is bonded to an atom ortho to the bond with ring A,
(3) ring D is benzene, and Z 1 or Z 2 is bonded para to the bond with metal M,
(4) at least one R A or R B comprises a moiety selected from at least two rings that are not fused together, partially or fully deuterated alkyl, or partially or fully deuterated cycloalkyl, or
(5) K is O or S; and
if condition (1), condition (2), condition (3), or condition (4) is true, then the compound has a formula selected from the group consisting of Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), and Ir(L A )(L B )(L C ), wherein L C is a bidentate ligand, wherein L A , L B , and L C are different from each other, and wherein L B is selected from the group consisting of
wherein:
T is B, Al, Ga, or In;
each of Y 1 to Y 13 is independently selected from the group consisting of C and N;
Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
each R a , R b , R c , and R d independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; the general substituents defined herein; and
any two adjacent R a , R b , R c , R d , R e and R f can be fused or joined to form a ring or form a multidentate ligand.
12 . A consumer product comprising an 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 having a structure of Formula I:
wherein:
ring A is a 6-membered aromatic ring;
ring D is a monocyclic or multicyclic fused ring system comprising one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;
K is selected from the group consisting of a direct bond, 0, and S;
R A represents zero, mono, or up to a maximum allowable substitution to its associated ring;
R D represents di or up to a maximum allowable substitution to its associated ring;
at least two adjacent R D form a structure of Formula II fused to D;
Z 1 is selected from the group consisting of O, S, Se, NR, and SiRR′;
Z 2 is N;
if ring D is benzene, then neither Z 1 nor Z 2 are fused to D at the carbon ring atom adjacent to the carbon ring atom that bonds to K;
each R A , R B , R D , R, and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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;
the ligand L A complexes to a metal M through the dashed lines to form a 5-membered chelate ring;
M is Ir;
M can be coordinated to other ligands;
L A can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
any two of R A , R B , R D , R, and R′ can be joined or fused to form a ring;
at least one of the following is true:
(1) ring D is a multicyclic fused ring system wherein the ring of said multicyclic fused ring system that is directly coordinated to M is a 6-membered carbocyclic ring, and wherein Formula II is directly fused to a 6-membered ring of said multicyclic fused ring structure that is not directly coordinated to M,
(2) ring D is benzene, and a Z 1 or Z 2 is bonded to an atom ortho to the bond with ring A,
(3) ring D is benzene, and Z 1 or Z 2 is bonded para to the bond with metal M,
(4) at least one R A or R B comprises a moiety selected from at least two rings that are not fused together, partially or fully deuterated alkyl, or partially or fully deuterated cycloalkyl, or
(5) K is O or S; and
if condition (1), condition (2), condition (3), or condition (4) is true, then the compound has a formula selected from the group consisting of Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), and Ir(L A )(L B )(L C ), wherein L C is a bidentate ligand, wherein L A , L B , and L C are different from each other, and wherein L B is selected from the group consisting of
wherein:
T is B, Al, Ga, or In;
each of Y 1 to Y 13 is independently selected from the group consisting of C and N;
Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
each R a , R b , R c , and R d independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, the general substituents defined herein; and
any two adjacent R a , R b , R c , R d , R e and R f can be fused or joined to form a ring or form a multidentate ligand.
13 . The compound of claim 1 , wherein ring D is a multicyclic fused ring system wherein the ring of said multicyclic fused ring system that is directly coordinated to M is a 6-membered carbocyclic ring, and wherein Formula II is directly fused to a 6-membered ring of said multicyclic fused ring structure that is not directly coordinated to M.
14 . The compound of claim 1 , wherein ring D is benzene, and Z 1 or Z 2 is bonded to an atom ortho to the bond with ring A.
15 . The compound of claim 1 , wherein at least one R A or R B comprises a moiety selected from at least two rings that are not fused together, partially or fully deuterated alkyl, or partially or fully deuterated cycloalkyl.
16 . The compound of claim 1 , wherein the compound has a formula selected from the group consisting of Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), and Ir(L A )(L B )(L C ), wherein L C is a bidentate ligand, wherein L A , L B , and L C are different from each other, and wherein L B is selected from the group consisting of
wherein:
T is B, Al, Ga, or In;
each of Y 1 to Y 13 is independently selected from the group consisting of C and N;
Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
each R a , R b , R c , and R d independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e , and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; the general substituents defined herein; and
any two adjacent R a , R b , R c , R d , R e , and R f can be fused or joined to form a ring or form a multidentate ligand.